Synthesis of some new pyrimidine and fused pyrimidine derivatives (Part 2).

6-Oxo-4(2-thienyl)-2-thioxo-1,3-dihydropyrimidine-5-carbonitrile (1) was synthesized and reacted with alkyl halides to give the S-alkyl compounds (2a,b), which reacted with phosphorous oxychloride to yield (3a,b). Reaction of 3a,b with phenyl-hydrazine, hydrazine hydrate, ammonia, acid hydrazides and thiourea leads to formation of the compounds (4a,b), the dihydrazino compound derivative (5), the amino compounds (7a,b), triazolopyrimidine derivatives (9a-d), and the mercapto compounds (10a,b), respectively. Treatment of (10a) with chloroacetone gave (11a), which condensed with benzaldehyde giving the tricyclic compound (12). Also (10b) reacted with ethyl chloroacetate followed by hydrolysis and cyclization yielded (14). Heating of (5) gave (6), which reacted with sodium nitrite and/or carbondisulphide and give (15) and (16), respectively.