Hydrochloric Acid → 4-Amino-2-chloro-6-(methylthio)pyrimidine-5-carbonitrile

Participants

Reaction Steps

Process for the production of 4-amino-2-chloro-5-cyano-6-(methylthio)pyrimidine of the formula: ##STR9## comprising reacting malononitrile with carbon disulfide in the presence of a strong base to obtain a dianion of dicyanodithioacetic acid of the formula: ##STR10## and then is methylating the dianion of dicyanodithioacetic acid of formula II with a methylating agent to obtain a dicyanoketene dimethyl thioacetal of the formula: ##STR11## condensing the dicyanoketene dimethyl thioacetal of formula III with cyanamide in the presence of a base to obtain an anion of 2-cyano-3-cyanamino-3-methylthio-acrylonitirile of the formula: ##STR12## and then the anion of 2-cyano-3-cyanoamino-3-methylthio-acrylonitrile of formula IV is cyclized in the presence of hydrochloric acid to obtain the 4-amino-2-chloro-5-cyano-6-(methylthio)pyrimidine.

Provenance & Evidence