Metallation studies with pyrimidines
Identifieur interne : 000F15 ( Istex/Corpus ); précédent : 000F14; suivant : 000F16Metallation studies with pyrimidines
Auteurs : Alan R. Katrizky ; Hector J. Salgado ; Amornsri Chermprapai ; Narayan K. PonksheSource :
- Journal of the Chemical Society, Perkin Transactions 1 [ 0300-922X ] ; 1982.
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Abstract
2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH2 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one forms a carbanion which undergoes dimerisation.
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DOI: 10.1039/P19820000153
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Soc., Perkin Trans. 1</title><idno type="ISSN">0300-922X</idno><idno type="eISSN">1364-5463</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="1982">1982</date><biblScope unit="volume">0</biblScope><biblScope unit="issue">0</biblScope><biblScope unit="page" from="153">153</biblScope><biblScope unit="page" to="158">158</biblScope></imprint><idno type="ISSN">0300-922X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0300-922X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Absolute etoh</term><term>Chbr</term><term>Crude product</term><term>Ethyl iodide</term><term>Etoh</term><term>General procedure</term><term>Glacial hoac</term><term>Methyl group</term><term>Methyl iodide</term><term>Mmhg</term><term>Mmol</term><term>Prism</term><term>Singlet</term><term>Spectral data</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Absolute etoh</term><term>Chbr</term><term>Crude product</term><term>Ethyl iodide</term><term>Etoh</term><term>General procedure</term><term>Glacial hoac</term><term>Methyl group</term><term>Methyl iodide</term><term>Mmhg</term><term>Mmol</term><term>Prism</term><term>Singlet</term><term>Spectral data</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH2 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one forms a carbanion which undergoes dimerisation.</div></front></TEI><istex><corpusName>rsc-journals</corpusName><keywords><teeft><json:string>mmol</json:string><json:string>etoh</json:string><json:string>prism</json:string><json:string>singlet</json:string><json:string>mmhg</json:string><json:string>spectral data</json:string><json:string>chbr</json:string><json:string>general procedure</json:string><json:string>absolute etoh</json:string><json:string>glacial hoac</json:string><json:string>methyl iodide</json:string><json:string>crude product</json:string><json:string>ethyl iodide</json:string><json:string>methyl group</json:string></teeft></keywords><author><json:item><name>Alan R. Katrizky</name></json:item><json:item><name>Hector J. Salgado</name></json:item><json:item><name>Amornsri Chermprapai</name></json:item><json:item><name>Narayan K. Ponkshe</name></json:item></author><language><json:string>eng</json:string></language><originalGenre><json:string>ART</json:string></originalGenre><abstract>2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH2 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one forms a carbanion which undergoes dimerisation.</abstract><qualityIndicators><score>5.686</score><pdfVersion>1.3</pdfVersion><pdfPageSize>576 x 756 pts</pdfPageSize><refBibsNative>false</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>302</abstractCharCount><pdfWordCount>3326</pdfWordCount><pdfCharCount>18864</pdfCharCount><pdfPageCount>6</pdfPageCount><abstractWordCount>30</abstractWordCount></qualityIndicators><title>Metallation studies with pyrimidines</title><genre><json:string>article</json:string></genre><host><title>Journal of the Chemical Society, Perkin Transactions 1</title><language><json:string>unknown</json:string></language><publicationDate>1982</publicationDate><issn><json:string>0300-922X</json:string></issn><eissn><json:string>1364-5463</json:string></eissn><volume>0</volume><issue>0</issue><pages><first>153</first><last>158</last><total>6</total></pages><genre><json:string>journal</json:string></genre></host><categories><inist><json:string>sciences appliquees, technologies et medecines</json:string><json:string>sciences biologiques et medicales</json:string><json:string>sciences medicales</json:string><json:string>cardiologie. appareil circulatoire</json:string></inist></categories><publicationDate>1982</publicationDate><copyrightDate>1982</copyrightDate><doi><json:string>10.1039/P19820000153</json:string></doi><id>0C923BA55EF4F8F2B4D737914BE75209BC03C45E</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/0C923BA55EF4F8F2B4D737914BE75209BC03C45E/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/0C923BA55EF4F8F2B4D737914BE75209BC03C45E/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/0C923BA55EF4F8F2B4D737914BE75209BC03C45E/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">Metallation studies with pyrimidines</title><respStmt><resp>Références bibliographiques récupérées via GROBID</resp><name resp="ISTEX-API">ISTEX-API (INIST-CNRS)</name></respStmt></titleStmt><publicationStmt><authority>ISTEX</authority><publisher scheme="https://publisher-list.data.istex.fr">The Royal Society of Chemistry.</publisher><availability><licence><p>This journal is © The Royal Society of Chemistry</p></licence><p scheme="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-Z6ZBG4DQ-N">rsc-journals</p></availability><date>1982</date></publicationStmt><notesStmt><note type="article" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</note><note type="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a">Metallation studies with pyrimidines</title><author xml:id="author-0000"><persName><forename type="first">Alan R.</forename><surname>Katrizky</surname></persName></author><author xml:id="author-0001"><persName><forename type="first">Hector J.</forename><surname>Salgado</surname></persName></author><author xml:id="author-0002"><persName><forename type="first">Amornsri</forename><surname>Chermprapai</surname></persName></author><author xml:id="author-0003"><persName><forename type="first">Narayan K.</forename><surname>Ponkshe</surname></persName></author><idno type="istex">0C923BA55EF4F8F2B4D737914BE75209BC03C45E</idno><idno type="ark">ark:/67375/QHD-DWT1HWH7-B</idno><idno type="DOI">10.1039/P19820000153</idno><idno type="ms-id">P19820000153</idno></analytic><monogr><title level="j">Journal of the Chemical Society, Perkin Transactions 1</title><title level="j" type="abbrev">J. Chem. Soc., Perkin Trans. 1</title><idno type="pISSN">0300-922X</idno><idno type="eISSN">1364-5463</idno><idno type="coden">JCPRB4</idno><idno type="RSC-sercode">P1</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="1982"></date><biblScope unit="volume">0</biblScope><biblScope unit="issue">0</biblScope><biblScope unit="page" from="153">153</biblScope><biblScope unit="page" to="158">158</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1982</date></creation><langUsage><language ident="en">en</language></langUsage><abstract><p>2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH2 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one forms a carbanion which undergoes dimerisation.</p></abstract></profileDesc><revisionDesc><change when="1982">Published</change><change xml:id="refBibs-istex" who="#ISTEX-API" when="2017-10-18">References added</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/0C923BA55EF4F8F2B4D737914BE75209BC03C45E/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="corpus rsc-journals not found" wicri:toSee="no header"><istex:xmlDeclaration>version="1.0" encoding="UTF-8"</istex:xmlDeclaration><istex:document><article type="ART" xsi:schemaLocation="http://www.rsc.org/schema/rscart38 http://www.rsc.org/schema/rscart38/rscart38.xsd" dtd="RSCART3.8"><metainfo><articletype code="ART" pubmedForm="research-article" headingForm="Papers" group="Paper" fullForm="Paper"></articletype></metainfo><art-admin><ms-id>P19820000153</ms-id><doi>10.1039/P19820000153</doi></art-admin><published type="print"><journalref><link>P1</link></journalref><volumeref><link>0</link></volumeref><issueref><link>0</link></issueref><pubfront><fpage>153</fpage><lpage>158</lpage><no-of-pages>6</no-of-pages><date><year>1982</year></date></pubfront></published><published type="subsyear"><journalref><title type="abbreviated">J. Chem. Soc., Perkin Trans. 1</title><title type="full">Journal of the Chemical Society, Perkin Transactions 1</title><title type="journal">Perkin Transactions 1</title><title type="display">Organic & Biomol. Chem + Perkin Trans. + Contemp. Org Synth.</title><sercode>P1</sercode><publisher><orgname><nameelt>The Royal Society of Chemistry</nameelt></orgname></publisher><issn type="print">0300-922X</issn><issn type="online">1364-5463</issn><coden>JCPRB4</coden><cpyrt>This journal is © The Royal Society of Chemistry</cpyrt></journalref><pubfront><fpage></fpage><lpage></lpage><no-of-pages></no-of-pages><date><year>1982</year></date></pubfront></published><art-front><titlegrp><title>Metallation studies with pyrimidines</title></titlegrp><authgrp><author><person><persname><fname>Alan R.</fname><surname>Katrizky</surname></persname></person></author><author><person><persname><fname>Hector J.</fname><surname>Salgado</surname></persname></person></author><author><person><persname><fname>Amornsri</fname><surname>Chermprapai</surname></persname></person></author><author><person><persname><fname>Narayan K.</fname><surname>Ponkshe</surname></persname></person></author></authgrp><abstract><p>2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1<it>H</it>)-ones can be acylated and alkylated at the α-CH<inf>2</inf> group. 1-Methyl-4,6-di-<it>p</it>-tolylpyrimidin-2(1<it>H</it>)-one forms a carbanion which undergoes dimerisation.</p></abstract></art-front><art-body><section type="PDFExtract"><title></title><p> 1982 153 MetaIlation Studies with Pyrimidines By Alan R. Katrizky,' Hector J. Salgado, Amornsri Chermprapai, and Narayan K. Ponkshe, School of Chemical Sciences, University of East Anglia, Norwich, NR4 7TJ, England and Department of Chemistry, University of Florida, Gainesville, Florida 3261 1, U.S.A. 2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1 H)-ones can be acylated and alkylated at the a-CH, group. 1 -Methyl- 4,6-di-p-tolylpyrimidin-2(1 H)-one forms a carbanion which undergoes dimerisation. As part of a larger study of heterocycle stabilised car- banions,l we have investigated pyrimidines : (a) 2- alkylamin0-4~6-diphenylpyrimidinesto attempt to gener- ate carbanions of type (9), and (b) 1-substituted 4,6-diphenylpyrimidin-2( lH)-ones to examine carbanions of type (18). </p><p>(3) R = H, R'= Me (4)R =H, R'= Et (5) R =H, R'= Pr" (6) R = Ph, R'= H (7) R = Me, R'= H Ph (81 Ph I c=oI C6H4Me-p (10) R'=Me (11) R'= Et (12) R'= Pi" SCHEME1 2-AZkyZamino~yrimidines.4,6-Diphenylpyrimidin-2(1H)-one (1) is converted by phosphoryl chloride into 2- chloro-4,6-diphenylpyrimidine(2).2 This reacts readily with primary and secondary amines (ethylamine, n-propylamine, n-butylamine, and N-methylaniline) to give the corresponding 2-alkylaminopyrimidines (3)-(6) (Table 1). The analogous 2-dimethylamino-derivative RCH,* NH* CONH2 (15 1 (13) Ar t Ph a; R = Ph (16) Ar = Ph (14) Ar = p-To1 b; R=H (17) Ar = P-TO~ Arck?'I I PhCHE PhCH-ii (20) Ar =Ph (18) Ar = Ph (2l) Ar = p-To1 (19) Ar = p-To1 E E a; H f; EtOCO b; D g; PhzCOH c; Ac h ;p-MeC6H4CHOH d; Bz i; Me e ;p-MeC6H4CO j; Et SCHEME2 (7) was obtained by ring synthesis from dibenzoyl- methane and NN-dimethylguanidine. </p><p>Structures of all the compounds were confirmed by their spectral data (Table 2). Treatment of the 2-alkylamino-4,6-diphenylpyrimi-dines (3)-(5) with lithium di-isopropylamide (LDA) gave the mono-anion (8), but not the dianion (9): subse-quent treatment with P-toluoyl chloride yielded amides (lo)-( 12)(Table3). Structures were confirmed by their spectral data (Table 4): in particular the low v(G0) excludes the possibility that the acyl group is attached to a cyclic nitrogen atom. </p><p>Use of excess LDA mainly gave the known NN-di-isopropyl-9-toluamide. 4,6-Diaryl-l-benzyZ~yrimidin-2(1H)-ones.-The diaroylmethanes (13)and (14) reacted with benzylurea (15a) to give the 4,6-diaryl-l-benzylpyrimidin-2(lH)- J.C.S. Perkin I TABLE1 Preparation of 2-alkylamino-4,6-diphenylpyrimidines(3)-( 7) Found (%) Required (%)Yield r---r-------7 R R M.p. ("C) (%) Crystal form Cryst. solvent C H N C H N H Me 66-68 49 Needles EtOH 78.2 6.1 15.1 78.5 6.2 15.3 H Et 96-99 51 Prisms EtOH 78.7 6.7 14.5 78.9 6.6 14.5 H Prn 58-61 58 Plates EtOH 78.8 6.8 13.7 79.2 7.0 13.8 Ph H 147-147.5 91 Fine needles 95% EtOH 81.8 5.8 12.4 81.9 5.7 12.5 Me H 131.5-132.5 30 Prisms EtOH 78.5 6.0 15.2 78.5 6.2 15.3 TABLE2 1.r. </p><p>a and 'H n.m.r. (6, 60 MHz) spectral data of 2-alkylamino-4,6-diphenylpyrimidines(3)-(7) N.m.r. A1.r. r 7 NH -N CH, R' Aromatic No. R R' (cm-') R (3) H Me 3 280 5.35 3.65 1.33 7.8 (1 H, bm) (2 H, qn) (3 H, t) (13 H, m) (4) H Et 3 250 5.4 3.5 1.5 1.0 7.8 (1 H, bm) (2 H, 9) (2 H, m) (3 H, t) (11H, m) (5) H Prn 3 280 5.9 centred at 0.9 1.4 7.8 (1 H, t) 3.35 (3 H, d) (4 H, m) (11 H, m) (2 H, bm) (6) Ph H 3.68 7.12-7.68 (3 H, m) (12 H, m)7.9-8.20 (4 H, m) (7) Me H 3.34 7.36-7.66 (6 H, s) (7 H, m)8.17-8.2 (4 H, m) a In CHBr,. b In CDC1,. s = singlet, bm = broad multiplet, t = triplet, q = quartet, qn = quintet, m = multiplet. TABLE3 Preparation of N-alkyl-N-(4,6-diphenylpyrimidinyl)-~-toluamides(lo)-( 12) Found (%) Required (%).A Yield r r-h-No. </p><p>R' M.p. ("C) (yo)Cryst. form Cryst. solvent C H N7 C H N (10) Me 128-132 60 Needles Ether-light 78.9 5.6 10.6 79.4 5.9 10.7 petroleum (b.p. 60-80 "C) (11) Et 135-138 55 Prisms EtOH 79.4 6.4 10.3 79.6 6.2 10.3 (12) PP 91-94 37 Needles 95% EtOH 79.5 6.5 9.9 79.8 6.5 10.0 TABLE4 1.r. a and 1H n.m.r. (6, 60 MHz) b spectral data of N-alkyl-N-(4,6-diphenylpyrirnidinyl)-~-toluamides(lo)-( 12) 1.r. N.m.r. 7(cm-1) ' INo. R' >=O P-ToluOyl N-CHt-R' AromaticI (10) Me 1655 2.27 4.42 1.4 7.4 (11) Et 1650 2.25 4.35 centred at 1.05 7.5 (3 H, s) (2 H, m) (3 H, t) (15H, m) (3 H, s) (2 H, t) 1.9 (3 H, t) (15 H, m) (2 H, m) (12) Prn 1650 2.28 4.37 1.o 1.65 7.5 (3 H, s) (2 H, t) (3 H, t) (4 H, m) (15 H, m) In CHBr,. </p><p>b In CDC1,. s = singlet, m = multiplet, t = triplet. ones (16) and (17) (cf. ref. 4). We have shown pre- form products (2Oc-j); methyl and ethyl iodide gave viously that 1-benzyl-4,6-diphenyl-2(1H)-pyridone (22) the alkylated derivatives (20i) and (2Oj) ; ethyl chloro- is converted by LDA into the lithio-derivative (23) which formate the ester (20f) ; acetyl, benzoyl, and 9-toluoyl reacts with electrophiles to form a-substituted products chloride the ketones (~OC),(20d),and (2Oe) ; p-tolualde-(24). We now find that lithio-derivatives (18) and (19) hyde and benzophenone the hydroxy-derivatives (20h) can be formed similarly; they show an intense blue and (20g). </p><p>Organolithium (19) reacted with methyl colouration. iodide to give the alkylated derivative (21i). All the The diphenyl carbanions (18) and (19) react with D,O compounds were characterised by their spectral data to form the deuteriated pyrimidinones (20b) and (21b). (Table 5). (1H)-one.-ReactionOrganolithium (18) adds to a variety of electrophiles to l-Methyl-4,6-di-p-toZyZ$y~imidin-2 1982 155 TABLE5 1.r.a and lH n.m.r. (6, GO MHz) b spectral data of 4,6-diaryl-l-benzylpyrimidin-2-ones(20)and (21) 1.r. (cm-’) 1H N.m.r.Lr-R 7 hr Alpha Pyridone Aromatic \ r--h--, No. substituent C=O OH C=O 5-H (s) 1’-H R (m)1645 6.70 5.2 (s) 7.52-7.05 (15 H)(204 H D 1650 6.70 5.2 (s) 7.05-7.52 (15 H) MeCO 1 640 1680 6.42 d 2.3 (s) 6.80-7.82 (16 H)ti::))(20d) PhCO 1650 1700 6.80 6.65 (s) 7.2-8.3 (20 H)(2oe) fJ-MeC,H,CO 1650 1 690 6.72 d 2.28 (s) 7.0-8.2 (20 €3) (20f) EtOCO 1650 1740 6.40 6.30 (s) 4.0 (in) 1.1 (t) 6.98-7.9 (15 H) (20g) Ph,COH 1650 3 %50 6.16 6.0 (s) 6.74-7.3 (25 H)(20h) p-MeC,H,CHOH 1 650 3 300 6.50 5.86 (d) e 5.45 (d)e 2.24 (s) 7.0-8.0 (14 H) (20i) Me 1650 6.90 5.5 (q) 1.6 (d) 7.2-7.8 (15 H) Et 1655 6.50 5.9 (m) 1.2 (m) 0.7 (t) 6.9-7.9 (15 H)I;?;) f H 1 650 6.60 5.2 (s) 7.9-7.1 (13 H) (21b) f D 1655 6.60 5.15 (s) 7.0-8.0 (13 H)(21i) f Me 1650 6.50 5.4 (q) 1.75 (d) 7.85-7.05 (13 H) a 111CHBr,. </p><p>6 In CDCI,. d = doublet, q = quartet, s = singlet, t = triplet, m = niultiplet. Integrates for 1 H. Over-lapped in the aromatic region. </p><p>e CH, doublet (J 10 Hz). f In addition two singlets (3 H each) are shown at 2.3 and 2.4 p.p.m. of N-methylurea (15b) with (14) yielded l-methyl-protons of the bridging methylene group were magnetic- pyrimidinone (25) which formed a deep red colouration ally non-equivalent and gave an AB system in both com- with LDA ; subsequent addition of electrophiles then pounds. In (28)the A-proton appeared at 6 4.75 and the merely gave recovered (25). Attempted use of n-butyl-€3-proton at 6 5.34 with Jgem 12 Hz. Similarly in (29) lithium as base afforded the addition product (30) ,which the A-proton appeared at 6 4.76 and the B-proton at 6 shows v(NH) 3 200 cm-l and v(C=O) 1 650 (broad). 5.41 with Jgem 14 Hz. In (28) and (29) the ,\‘-methyl group (1’â€� protons) gave a singlet at 6 1.70; in (28) the incorporated methyl gave a singlet at 6 2.5 and in (29), the diastereotopic methylene protons of the incorporated a. </p><p>a.-LiNPrit E+ Ph Ph Ph 0I: I PhCH2 PhCH -ti WCHY (22) (23) (24) Me CHr Li In the 1H n.m.r., the n-butyl group signals occur at 0.84 (3 H, t), 1.3 (4 H, m), and 1.82 p.p.m. (2 H, m). The C-(25) (26) methyls resonate as two 3-H singlets near to 2.8 p.p.m. The heterocyclic ring olefinic hydrogens form a 2 Hz split doublet at 4.87 p.p.m. coupled (J 2 Hz) with the N-H proton (broad doublet at 5.74 p.p.m.). These spectral data appear to support a 1,2-addition to C=N to give (30) rather than 1,4-addition to C=C-C=N to give an isomer, but we have not rigorously excluded the isomeric RIstructure. </p><p>Sodium borohydride reduces pyrimidin-2- -ones to dihydro- and tetrahydro-derivativesJ5and this provides an analogy for the formation of (30). However, reaction of (25) with 2,2,6,6-tetramethyl- piperidyl-lithium (LTMP) followed by methyl iodide formed (28) by a lJ6-addition of the lithio-derivative (26) to a second molecule of (25) to give anion (27). Similarly addition of ethyl iodide produced (29). The structures (28) and (29) are based on spectral evidence: both (28) and (29) showed v(C=O) (pyrimidin-one) at 1650 cm-l (broad). In the 1H n.m.r. spectra, the ring proton of the undisturbed pyrimidinone ring in (28) gave a singlet at 6 6.56 (5’-H) and at 6 6.62 in (29) (5'-H) . The corresponding signal in the pyrimidinone (25)was at 6 6.64. </p><p>In the modified pyrimidinone ring of Me (28)and (29),the 5-H signal shifted upfield, resonating as (30) a singlet at 6 4.54 and 4.56 respectively. The prochiral SCHEME3 ethyl formed two sextets at 6 3.10 and 6 3.90 with Jpic 7 Hz and Jgem 14 Hz. The methyl group displayed a triplet at 6 0.78 p.p.m. The Aromatic protons in both (28)and (29)displayed a multiplet in the range 6 8.0-7.0. In the 13C n.m.r. spectra,with off-resonance C-H information, for both (28) and the undisturbed pyrimidinone carbonyl carbon gave a sing1et at 169.19 and at 169.23 respectively [Cf. l69-3l in (25)1whilst the modified pyrimidinone carbony1 resonated at 6 160.27 and 160.12. The aromatic carbons displayed a series of J.C.S. Perkin I HA-100 (100 MHz) n.m.r. </p><p>spectrometers, 13C n.m.r. spectra at 25.05 MHz on a Jeol FX-100 Fourier transform spectro- photometer, and high-resolution mass spectra on an AEI MS-9 'pectrometer. 4,6-DiphenyzpYrimidin-2-one (l).-Dibenzoylmethane (5 g, 22.3 mmol), urea (2.0 g, 33.4 mmol), toluene-P-sulphonic acid (5.75 g, 33.4 mmol), and glacial HOAc (15 ml) were heated under reflux for 48 h and neutralised with aqueous NaOH (12%). The product separated; it was collected, washed with water, dried, and crystallised (EtOH) (m.p. 237-239 "C) (4.20g, 15%) [lit.,zb m.p. 237-239 "C]. TABLE 6 13C N.m.r. spectra a of 1,3-disubstituted 1,2,3,6-tetrahydro-6-( 1,2-dihydro-2-oxo-4,6-di-p-tolylpyrimiclinylmethyl)-4,6-di-p-tolylpyrimidin-2( lH)-ones (28) and (29) Aliphatic region A-7Carbonyl Aromatic Olefinic region r-region (s) region r~-Aryl-CH,Compd. </p><p>r~.-, Unassigned 5-C 5'-C7 6C 1"-C 1" '-C (9) 3-N-R -__-7r---7no. 2-CO 2'C0 multiplet (4 (4 (s) (t) (9) r (28) 169.19 160.27 159.68-126.64 105.30 103.60 (28) 67.15 48.53 30.35 21.48 21.38 21.28 20.91 33.08 (9) (29) 169.23 160.12 159.39-126.55 105.20 103.84 (29) 67.73 48.04 30.26 21.50 21.39 21.19 20.90 39.27 (t) 14.96 (4) In CDC1, with SiMe, as internal reference. lines in the range 159.68-126.55 (Table 6). The 5 and 5' ring carbons gave doublets at 6 105.30 and 6 103.60 in (28) and at 6 105.20 and 6 103.84 in (29) [cf. 102.44 in (25)]. In the aliphatic region, the bridging methylene carbon gave a triplet at 48, the 6-quaternary carbon a singlet at 67, and the N-methyl, a quartet at 30 (Table 6). The inserted methyl in (28)gave a quartet at 6 33.08 whilst in (29), the inserted ethyl gave a triplet at 6 39.27 and a quartet at 14.96. </p><p>The C-methyl group gave 4 quartets in the range 6 21.50-20.90 (Table 6). High-resolution mass spectroscopy showed the mole- cular ion peak at m/e 594.29 (0.12%) for (28) and at TT?-xo Me (31) R= Me (32) R= Et 608.31 (0.05%)for (29). Both (28) and (29)underwent a retrosynthetic expulsion of the oxopyrimidinylmethyl fragment to give the observed base peaks at m/e 305.16 (100%) (31) and 319.17 (100%) (32) respectively. EXPERIMENTAL M.p.s were measured on a Reichert hot-stage melting point apparatus and are uncorrected. </p><p>1.r. spectra were recorded in CHBr, on a Perkin-Elmer 297 spectrophotometer, lH n.m.r. spectra on Perkin-Elmer R12 (60 MHz) and Varian 2-Chloro-4,6-dipheny@yrimidine (2) (47%), had m.p. 113-113.5 "C [lit.,2a m.p. 115-116 "C]. General Procedure for the Preparation of 2-Amino-4,6-diphenylpyrimidines (3)-( 6) .-2-Chloro-4,6-diphenylpyri-midine (2) and the appropriate amine were heated under reflux in absolute EtOH for 2 h. [For the preparation of (3), dry EtNH, gas was bubbled through a solution of (2) in absolute EtOH and for (6), the reactants were heated in the absence of absolute EtOH]. Evaporation (100 "C/15 mmHg) gave the crude product, which was washed with water and crystallised (see Table 1). 2-Dirnethylamino-4,6-diphenylpyrimidine(7).-Dibenzoyl-methane (1 g, 4.46mmol), NN-dimethylguanidine, HCl(1 g, 8.16 mmol), and K2C03(0.6 g, 4.3mmol) were heated under reflux in EtOH (10 ml) €or 2 h then extracted with CH,Cl, (50 ml) and the extracts washed with H,O (20 ml). The dried (MgSO,) extracts on evaporation (100 "C/15 mmHg) furnished the product, which was crystallised (see Table 1). </p><p>General Procedure for the Preparation of Amides (10)-(12). -To LDA (1mmol) in dry THF (5 ml) [prepared by adding dropwise n-butyl-lithium in hexane (1 mmol) to di-isopropyl- amine (1 mmol) at 0 to -5 "C under Na]cooled to 0 to -5 "C was added 2-alkylaminopyrimidine (3)-(5) (0.5 mmol) in dry THF (2 ml). After 0.5 h at 0 to -5 "C, p-toluoyl chloride (1 mmol) in dry THF (2 ml) was added. </p><p>Stirring was continued for a further 4 h at 20 "C,water (5ml) was then added and the solution extracted with CH,Cl, (30 ml) ; the extracts were washed with aqueous NaHCO, (lo%, 10 ml) followed by H,O (10 ml). The dried (Na,SO,) extracts on evaporation (100 "C/15 mmHg) gave the crude product as a yellowish oil which solidified slowly and crystallised from the appropriate solvent (Table 3). Purification of the mother- liquor afforded NN-di-isopropyl-p-toluamide as the by-product, m.p. 84 "C [lit.,, m.p. 85-86 "C] as colourless plates [toluene-light petroleum (b.p. 40-60 "C)]. l-BenzyZ-4,6-diphenylpyrimidin-2(1H)-one (20a) .-Diben- zoylmethane (5.0 g, 20 mmol), benzylurea (4.8 g, 32 mmol), and toluene-p-sulphonic acid (7.6 g, 40 mmol) in glacial HOAc (8 ml) were heated at reflux for 36 h. </p><p>Cooling and treatment with aqueous (50%) EtOH gave the pyyimidinone which crystallised from 95% EtOH as prisms (5.0 g, 68%), m.p. 164-165 "C (Found: C, 81.3; H, 5.4; N, 8.3. Cz3-H,,N,O requires C, 81.6; H, 5.3; N, 8.3%). l-BenzyZ-4,6-di-p-tolylpyvimzdin-2(1H)-one (2 la) .-Di-p- toluoylmethane (1.O g, 4 mmol), benzylurea (0.95 g, 6 mmol), and toluene-p-sulphonic acid (1.4 g, 7 mmol), in HOAc (1 ml) were heated at reflux for 36 h. Work-up as described for (20a) gave the pyvimidinone (2la) (0.9g, 62%) as needles from 95% EtOH, m.p. 209-210 "C (Found: C, 81.9; H, 6.1; N, 7.6. C,,H,,N,O requires C, 82.0; H, 6.0; N, 7.6%). l-MethyZ-4,6-di-p-toZyZpyvimidin-2(1H)-one (25) .-Di-p- toluoylmethane (5.0 g, 19 mmol), methylurea (3.1 g, 40 mmol), and toluene-p-sulphonic acid (7.2 g, 37 mmol) in HOAc (9 ml) were heated at reflux for 36 h. </p><p>Work-up as described for (20a) gave the pyvimidinone (25) (3.5 g, 61%)) as needles from 95% EtOH, m.p. 197-199 "C (Found: C, 78.7; H, 6.3; N, 9.6. C,,H,,N,O requires C, 78.6; H, 6.2; N, 9.6%); v~,,,~(CHBr,) 1 645 cm-l (GO) ; 6 (CDCl,) 7.98- 7.22 (8 H, m), 6.70 (1 H, s), 2.40 (3 H, s), 2.39 (3 H, s), and 3.40 (3 H, s). General Pvoceduve for tlze L-ithiation and Alkylation of 4,6-DiavyZ- l-benzyZpyrinzidin-2( 1H)-ones.-LDA (3.0 mmol) was prepared by adding dropwise di-isopropylamine (0.3 g, 3.0 mmol) to n-butyl-lithium in hexane (3.1 ml, 3.0 mmol of 0.96~)at -200 "C under N,. </p><p>Stirring of the mixture was continued until it became cloudy when dry THF (6 ml) added; the whole was then cooled to -76 "C and 4,6-diaryl- l-benzylpyrimidin-2-one (3.0 mmol) in dry THF (20 ml) was added. After 40 min at -76 "C, the electrophile (3.0 mmol) in dry THF (5 ml) was added. Stirring was continued for 1h at -76 "C and for a further 10 h at 20 "C. Water (1ml) was then added and the solvent removed at 40-50 OC/20 mmHg. The residue in CH,Cl, (70 ml) was washed with saturated aqueous NaCl (30 ml) and water (30 ml) and then dried (Na,SO,), and evaporated at 40-50 "C/20 mmHg. The product was separated by crystallisation [CHCl,-light petroleum (b.p. 60-80 "C)], or prep. t.1.c. and further re- crystallised from the appropriate solvent. </p><p>The following compounds were prepared according to the 157 plates from toluene, m.p. 170-170.5 "C (Found: C, 81.7; H, 5.5; N, 7.9. C,,H,,N,O requires C, 81.8; H, 5.7; N, 7.9%); 1-(a-ethy ZbenzyZ) -4,6-diphenyZpyrimidin-2(1H) -one (2Oj) (33%) (isolated by prep. t.l.c.), prisms from 95% EtOH, map. 218 "C (decomp.) (Found: C, 81.8; H, 6.3; N, 7.6. C,,H,,N,O requires C, 81.9; H, 6.0; N, 7.6%): 1-(a-deuteriobenzyl)-4,6-di-p-tolyZ~yvim~din-2(1H)-one (2 lb) (85y0),needles from 95% EtOH, m.p. 207-210 "C (Found: C, 81.5; N, 7.6. C,,H2,DN,0 requires C, 81.7; N, 7.6%); l-(a-methyZbenzyZ)-4,6-di-p-tolyZ~y~imidin-2(1H)-one (2li) (95y0), prisms from 95% EtOH, m.p. 186.5-187 "C (Found: C, 81.9; H, 6.5; PI;, 7.3. C,,H,,N,O requires C, 81.7; H, 6.3; N, 7.3%). </p><p>4-n-ButyZ-3,4-dihydvo-4,6-di-p-toZylpyvimidin-2(1H)-one (30).-To l-methyl-4,6-di-p-tolylpyrimidin-2(1H)-one (25) (1.0 g, 3.4 mmol) in dry THF (20 ml) at 0 "C, under N,, n-butyl-lithium (0.22 g, 3.4 mmol) was added. Stirring was continued for 1 h at 0 "C and for a further 0.5 h at 20 "C. Water (1ml) was added and the solvent removed at 30-40 "C/20 mmHg. The residue in EtOAc (50 ml) was washed with water (2 x 25 ml), dried (Na,SO,), and evaporated at 30-40 "C/20 mmHg. Prep. t.1.c. [EtOAc-light petroleum (b.p. 60-80 "C) (65: 35)] gave the tztZe compound (0.5 g, 42%) as needles (EtOH), m.p. 147-147.5 "C (Found: C, 79.1; H, 8.3; N, 8.1. C,,H,,N,O requires C, 79.3; H, 8.0; N, 8.0%); vmax. (CHBr,) 3 200 (N-H) and 1 650 cm-' (GO); 8 (CDC1,) 7.3-7.0 (8 H, m), 5.74 (1 H, d, J 2 Hz), 4.87 (1 H, d, J 5 Hz), 2.8 (3 H, s), 2.3 (3 H, s), 2.28 (3 H, s), 1.82 (2 H, m), 1.3 (2 H, m), and 0.84 (3 H, t, J 7 Hz). </p><p>3,6-Dihydro- 1,3-dimethyl-6- (1,2-dihydro-2-0~0-4,6-di-p-toZy Zpyvimidinylmethyl) -4,6-di-p-tolylpyrimidin-2(1H) one (28).-LTMP (4.5 mmol) was prepared in situ from n-butyl- lithium (2.86 ml, 4.5 mmol of 1.0~) and 2,2,6,6-tetramethyl- piperidine (0.63 g, 4.5 mmol), under N, at -20 "C. Dry THF (6 ml) was added, the whole cooled to -76 "C, and 1-methyl-4,6-di-p-tolylpyrimidin-2(1H)-one (1.O g, 3.5 mmol) in dry THF (25 ml) added. After 45 min, Me1 (0.6 g, 4.9 mmol) was added, stirring continued for 1 h at -76 "C, and general procedure : 1-(a-deuteriobenzyZ)-4,6-diphenyZpyvimi-for a further 12 h at 20 "C. </p><p>Water (1 ml) was then added, din-2(1H)-one (20b) (goyo),prisms from EtOH, m.p. 160- the solvent removed at 40-50 "C/20 mmHg, and the residue 161 "C (Found: C, 81.5; N, 8.2. C,,H,,DN,O requires C, taken up in CH,Cl, (60 ml), washed with H,O (30 ml), and 81.4; N, 8.2./,) ; l-(a-acetylbenzyl)-4,6-diphenyZpyviunidin-dried (anhydrous Na,SO,). The CH,Cl, solution was 2(1H)-one (20c) (48y0), plates from EtOH, m.p. 184-185 "C (Found: C, 78.7; H, 5.7; N, 7.4. C25H,,N,0, requires C, 78.9; H, 5.3; N, 7.4%) ; l-(oc-benzoylbenzyZ)-4,6-diphenyl-pyrimidin-2( 1H)-one (20d) (52y0), plates from EtOH, m.p. 168-170 "C (Found: C, 81.4; H, 5.0; N, 6.3. C,,H,,N,O, requires C, 81.4; H, 5.0; N, 6.3%); 4,6-diphenyl-l-[a-(4- toZuoyZ)benzyZ]py~~inzidin-2(1H)-one (20e) (54y0), plates from EtOH, m.p. 140-142 "C (Found: C, 81.2; H, 5.6; N, 6.0. </p><p>C,,H,,N,O, requires C, 81.6; H, 5.3; N, 6.1%); 1-(a-ethoxycarbonyZbenzy1)-4,6-diphenylpyvimidin-2(1H)-one (20f) (35%) (isolated by prep. t.l.c.), prisms from 95% EtOH, m.p. 228-230 "C (Found: C, 76.0; H, 6.8; N, 5.3. C26-H22NZO3 requires C, 76.1; H, 6.8; N, 5.3%); 1-(2,2-diphenyl-2-hydroxy-1-phenyl)ethyZ-4,6-diphenyZpyvimidin-2( lH)-one (20g) (20y0),prisms from 95% EtOH, map. 229 "C (decomp.) (Found: C, 82.7; H, 5.4; N, 5.3. C3,H,,N20, requires C, 83.0; H, 5.4; N, 5.4%) ; 1-[2-hydroxy-2-(4-methylpheny1)-l-phenyZ]ethyl-4,6-diphenylPyrimidin-2(1H)-one (20h) (40%) (isolated by prep. t.l.c.), prisms from 95% EtOH, m.p. </p><p>230 "C (decomp.) (Found: C, 81.6; H, 5.7; N, 6.2. C,,H,,N,O, requires C, 81.2; H, 5.7; N, 6.ly0); 1-(a- methyZbenzyZ)-4,6-di~henyl~yrimidin-2(1H)-one (20i) (40y0), evaporated at 40-50 "C/20 mmHg. Prep. t.1.c. [EtOAc- light petroleum (b.p. 60-80 "C) (55:45)] gave the litle compound (0.11 g, 10%) as prisms, m.p. 286.5-289 "C (EtOH) (Found: C, 78.8; H, 6.5; N, 9.2. C,,H,,N,O, requires C, 78.8; H, 6.4; N, 9.4%); vmax. (CHBr,) 1 650 cm-l (GO); 6 (CDCl,) 7.92-7.00 (16 H, m), 6.56 (1 H, s), 5.36 (1 H, d, J 12 Hz), 4.75 (1H, d, J 12 Hz), 4.54 (1 H, s), 2.5 (3 H, s), 2.31 (3 H, s), 2.28 (3 H, s), 2.22 (3 H, s), 2.19 (3 H, s), and 1.68 (3 H, s); m/e 594.29 (M+*,0.12), 305.16 (loo), 261.15 (0.81), and 132.08 (12.48). 3-Ethyl- 3,6-dihydvo- l-methyl-2-oxo-6- (1,2-dihydvo-2-oxo-4,6-di-p-toZyZpyrimidinylmethyl)-4,6-di-p-toZyZpyrimidin-2( 1H) -one (29).-l-Methyl-4,6-di-p-tolylpyrimidin-2(1 H)- one (1.0 g, 3.5 mmol) in THF (25 ml) was added to a solution [THF (10 ml)] of LTMP (4.5 mmol) (prepared as above) at -76 "C. </p><p>After 45 min., EtI (0.75 g, 4.8 mmol) was added, stirring continued for 1h at -76 "C and for a further 12 h at 20 "C. Work-up of the reaction was as above. Prep. t.1.c. separation [EtOAc-light petroleum (b.p. 60-80 "C) (55 : 45)] gave the title compound (0.163 g, 16%) as yellow prisms, m.p. 250-252 "C (PhCH,) (Found: C, 78.8; H, 6.5; N, 9.2. C4,H,,N,O2 requires C, 78.9; H, 6.6; N, 9.2%): vmx, (CHBr,) 1650 cm-1 (GO); 6 (CDCl,) 8.0-7.0 (16 H, m), 6.64 (1 H, s),5.34 (1 H, d, J 12 Hz), 4.76 (1 H, d, J 12 Hz),4.56 (1 H, s), 3.90 (1 H, sextet), 3.10 (1 H, sextet), 2.36 (6 H, s), 2.26 (3 H, s), 2.24 (3 H, s), 1.70 (3 H, s), and 0.78 (3 H, t); nz/e 608.31 (&I+,0.05),319.17 (loo), 305.16 (2.22),and 132.08 (2.82). </p><p>We thank the Leverhulme Foundation for a Fellowship (to N. I<. P.)and the Consejo Nacional de Ciencia y Tecnologia (Mexico) for a scholarship (to H. J. S. 2.). [1/188 RPCP~~~P~,9th February, 19811 J.C.S. Perkin I REFERENCES 1 (a) A. R. Katritzky, N. E. Grzeskowiak, T. Siddiqui, C. Jayaram, and S. N. Vassilatos, J. Chem. Res., in thepress; (b)A. R. Katritzky, J. Arrowsmith, Zakaria bin Bahari. C. Jayaram, T. Siddiqui, and S. Vassilatos, J. Chem. Soc., Perkzn Trans. 1, 1980, 2851; (c) A. R. Katritzky, N. E. Grzeskowiak, H. J. Salgado,and Zakaria bin Bahari, Tetrahedron Lett., 1980, 21, 4451. (a)CIBA Ltd., Fr. P. 1,396,68411965 [Chem. Abstr., 1965, 63, 9965dl; (b)V. P. Mamaev, Biol. Akt. Socdzn., Akad Nauk SSSH, 1965, 38, [Chem.Abstr., 1965, 63, lSOSlf].R. E. Ludt, J. S. Griffiths, K. N. McGrath, and C. R. Hauser, J. Org. Chem., 1973, 38, 1668.* G. E. Hardtmann and F.G. Iiathawala, Ger. I-’. P,O56,406/ 1971 [Cheun. Abstr., 1971, 75, 6381:%m]. 5 C. Kashima, Y. Yokota, 7’. Nishio. and A. Katoh, Fletrm-cycles, 1980, 14, 120. </p></section></art-body></article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Metallation studies with pyrimidines</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Metallation studies with pyrimidines</title></titleInfo><name type="personal"><namePart type="given">Alan R.</namePart><namePart type="family">Katrizky</namePart></name><name type="personal"><namePart type="given">Hector J.</namePart><namePart type="family">Salgado</namePart></name><name type="personal"><namePart type="given">Amornsri</namePart><namePart type="family">Chermprapai</namePart></name><name type="personal"><namePart type="given">Narayan K.</namePart><namePart type="family">Ponkshe</namePart></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="ART" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D"></genre><originInfo><publisher>The Royal Society of Chemistry.</publisher><dateIssued encoding="w3cdtf">1982</dateIssued><copyrightDate encoding="w3cdtf">1982</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract>2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1 -benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH2 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one forms a carbanion which undergoes dimerisation.</abstract><relatedItem type="host"><titleInfo><title>Journal of the Chemical Society, Perkin Transactions 1</title></titleInfo><titleInfo type="abbreviated"><title>J. Chem. Soc., Perkin Trans. 1</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><originInfo><publisher>The Royal Society of Chemistry.</publisher><dateIssued encoding="w3cdtf">1982</dateIssued></originInfo><identifier type="ISSN">0300-922X</identifier><identifier type="eISSN">1364-5463</identifier><identifier type="coden">JCPRB4</identifier><identifier type="RSC-sercode">P1</identifier><part><date>1982</date><detail type="volume"><caption>vol.</caption><number>0</number></detail><detail type="issue"><caption>no.</caption><number>0</number></detail><extent unit="pages"><start>153</start><end>158</end><total>6</total></extent></part></relatedItem><identifier type="istex">0C923BA55EF4F8F2B4D737914BE75209BC03C45E</identifier><identifier type="ark">ark:/67375/QHD-DWT1HWH7-B</identifier><identifier type="DOI">10.1039/P19820000153</identifier><identifier type="ms-id">P19820000153</identifier><accessCondition type="use and reproduction" contentType="copyright">This journal is © The Royal Society of Chemistry</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-Z6ZBG4DQ-N">rsc-journals</recordContentSource><recordOrigin>The Royal Society of Chemistry</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/0C923BA55EF4F8F2B4D737914BE75209BC03C45E/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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