SYNTHESIS OF [1,4]DITHIINO[2,3-d]PYRIMIDINE-6-CARBONITRILE DERIVATIVES VIA THE REACTION OF 2-[(4-CHLOROPYRIMIDIN-5-YL)SULFANYL]ACETONITRILES WITH CARBON DISULFIDE

摘要

An efficient procedure has been developed for the preparation of 7-(alkylsulfany1)[1,4]dithiino[2,3-d]pyrimidine-6-carbonitrile derivatives from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP). 2-{[4-Chloro-2(methylsulfanyl)pyrimidin-5-yl]sulfany}acetonitriles are prepared via the reaction of the 5-lithio derivative of DCSMP with sulfur and then 2-bromoacetonitrile. These can be converted into the desired products on treatment with carbon disulfide in the presence of sodium hydride followed by alkyl halides. This is the first construction of the [1,4]dithiino[2,3-d]pyrimidine structure.