Nucleophilic Substitution in Some 5-Chloropyrimidines. Synthesis and Properties of Condensed Pyridopyrimidines

Reaction of hetarylacetonitriles 1 with 5-chloro-2-(methylsulfonyl)-4-pyrimidinecarbonyl chloride affords a series of new ketonitriles 3e–h. The reactions of compounds 3 with aliphatic amines were studied. In the reaction of 3c, d, g with aliphatic amines the replacement of methylsulfonyl group took place to give products 4. In the reaction of 3a with aliphatic amines 3-NR1R2-5-oxo-5H-pyrimido-[4,5-c]quinolizin-6-yl cyanides 5a–d were formed. Compounds 3 cyclized into fused pyridopyrimidines 6–10 in the presence of Et3N and the displacement of methylsulfonyl group in 6, 7, 9 by amines was investigated.