Simple and efficient synthesis of new N(3)-, O- and S-substituted 2-methylthio-6-phenylpyrimidin-4(3H)-one based derivatives

Abstract

Reactions of sodium salt of 2-methylthio-6-phenylpyrimidin-4(3H)-one with chloroacetone, ω-bromoacetophenone and methyl bromoacetate in different solvents were studied. Regioselective N(3)-alkylation took place in tetrachloromethane at reflux, while in dimethylformamide at ambient temperature O-acylmethyl derivatives were obtained. 2-Methylthio-6-phenylpyrimidine-4(3H)-thione reacted with chloroacetone and ω-bromoacetophenone in a sodium methoxide–methanol solution to give the corresponding S-substituted derivatives. Oxidation reactions of the resulting N(3)-, O- and S-acylmethyl derivatives with hydrogen peroxide in acetic acid were discussed.