Abstract
Some analogs of toxopyrimidine with ethyl group attached to 2 position of the pyrimidine ring, were prepared. The synthesis of 2-ethyl-4-amino-5-hydroxymethylpyrimidine (III) started with the condensation of propioamidine with 2-methoxyethoxymethyl-3-ethoxypropionitrile to yield 2-ethyl-4-amino-5-propioamidomethylpyrimidine (I), which gave (III) through 2-ethyl-4-amino-5-aminomethylpyrimidine (II). Condensing propioamidine with 2-methoxymethylene-3-ethoxypropinitrile afforded 2-ethyl-4-amino-5-ethoxymethylpyrimidine (IV) which yielded 2-ethyl-4-amino-5-bromomethylpyrimidine (V) on treatment with hydrobromic acid. Catalytic hydrogenolysis of (V) gave the 5 methyl-derivative (VI). 2,5-Diethyl-4-amino-6-hydroxypyrimidine (VII) was prepared by condensing propioamidine with α-cyanobutyrate. Upon chlorination with phosphorus oxychloride and phosphorus pentachloride, (VII) gave the 6-chloro-derivative (VIII), which was treated to give 2,5-diethyl-4-aminopyrimidine by catalytic hydrogenolysis. Biological action of these compounds on animals or microbes will be reported elsewhere.
