W. Zielinski et M. Mazik, SYNTHESIS OF 4-AMINOPYRIMIDINE DERIVATIVES VIA REACTION OF N-STYRYLACETIMIDOYL CHLORIDES WITH CYANAMIDE, Polish Journal of Chemistry, 67(6), 1993, pp. 1099-1104
The reaction of cyanamide with N-(2-phenyl-1-methylvinyl)acetimidoyl c
hloride (2) and its derivatives substituted at the benzene ring was st
udied. At the first stage, linear products like -3,5-dimethyl-6-phenyl
-2,4-diaza-1,3,5-hexatrienes (6) were obtained. They underwent cycliza
tion to 4-amino-2,6-dimethyl-5-phenylpyrimidines (8) with good yields.
The mechanism of the reaction has been discussed basing on the net at
omic charges determined by MNDO method for the substrates and intermed
iate products and the experimental data.