A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Abstract

A convenient two-step synthesis of 2-trichloromethyl-4-chloropyrimidines starting from 2-trichloromethyl-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared in one pot synthesis by a sequential acylation/intramolecular cyclization reaction between 2-trichloromethyl-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 2-trichloromethyl-4-chloropyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.