Recyclization reactions of 1-alkylpyrimidinium salts

Ruben S Vardanyan, Gevork G. Danagulyan, Armen D. Mkrtchyan, Victor J Hruby

Research output: Contribution to journalArticle

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Abstract

The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C - C recyclizations: 2-benzyl-4-benzylamino-5- carbamoylpyrimidine ( 7 ) and the benzylimine of 4-amino-2-benzyl-6- benzylaminopyrimidine- 5-carbaldehyde ( 8 ). The reaction of 2-amino-1,4-dimethyl-5- ethoxycarbonylpyrimidinium iodide ( 10 ) with KOH ethanolic solution gave a single product of C - C-recyclization: 2-amino- 5-acetyl-4-hydroxypyrimidine ( 11 ).

Original languageEnglish (US)
Pages (from-to)129-133
Number of pages5
JournalHeterocyclic Communications
Volume17
Issue number3-4
DOIs
Publication statusPublished - Sep 2011

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Keywords

  • Pyrimidinium salt
  • Recyclization

ASJC Scopus subject areas

  • Organic Chemistry

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