Uracil Derivatives and Related Compounds. II. Alkylation of 6-Methyl-2-thiouracil Derivatives.

Abstract

The methylation of 6-methyl-2-thiouracil with dimethyl sulfate gave 3, 6-dimethyl-and 1, 6-dimethyl-2-methylthio-4-pyrimidone. The alkylation of 6-methyl-2-methylthio-4-pyrimidone with alkyl halide, however, gave both 3-alkyl-6-methyl-2-methylthio-4-pyrimidone and 4-alkoxy-6-methyl-2-methylthiopyrimidine. The compounds obtained above were hydrolyzed to afford 3-alkyl-6-methyluracils and 6-methyluracil. 4-Alkoxy-6-methyl-2-methylthiopyrimidine was also synthesized from 4-chloro-6-methyl-2-methylthiopyrimidine and sodium alkoxide.