Studies on the some heterocyclic pyrimidine derivatives of nitrogen. II. Syntheses of pyrimidines

Abstract

Five kinds of pyrimidine derivatives (VII) substituted in 2-position with phenyl, o-tolyl, p-tolyl, p-nitrophenyl, and p-bromophenyl groups were prepared, following the synthesis of 2-amino-4-methyl-5-ethoxycarbonylpyrimidine (I). 2-Ethoxymethyleneacetoacetate (III) was prepared from ethyl acetoacetate. Five kinds each of nitriles (IV), imidoethers (V), and amidine base hydrochlorides (VI) were prepared from aromatic primary amines such as aniline, o-toluidine, p-toluidine, p-nitroaniline, and p-bromoaniline. Condensation of the amidines (VI) with the ester (III), in the presence of sodium ethoxide as the condensation agent, resulted in smooth reaction to afford the corresponding esters (VII: R=C2H5). Hydrolysis of these esters (VII) by the usual method gave the corresponding free salts (VII: R=H). In the series of this work, condensation of acetamidine hydrochloride and the ester (III) failed to afford the pyrimidine derivative.