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Short Paper | Regular issue | Vol 98, No. 1, 2019, pp.105-113
Published online, 18th December, 2018
DOI: 10.3987/COM-18-14012
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

Kazuhiro Kobayashi,* Kota Yamasaki, Daiki Fujiwara, Kazuma Nozaki, Hidetaka Hiyoshi, and Kazuto Umezu

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


An efficient procedure has been developed for the preparation of 7-(alkylsulfanyl)[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]sulfanyl}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.