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Open AccessFeature PaperCommunication

Synthesis of 2-Cyanopyrimidines

Department of Life Sciences, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus
Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1086;
Received: 26 September 2019 / Revised: 17 October 2019 / Accepted: 21 October 2019 / Published: 22 October 2019
4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to 4-chloro-6-methoxypyrimidine-2-carbonitrile (13) and 4,6-dimethoxypyrimidine-2-carbonitrile (12), respectively, after oxidation to sulfones and displacement of the sulfinate group with KCN. 4,6-Dimethoxypyrimidine-2-carbonitrile (12) was chlorinated with NCS to give 5-chloro-4,6-dimethoxypyrimidine-2-carbonitrile (10) in 53% yield. All new compounds were fully characterized. View Full-Text
Keywords: heterocycle; pyrimidine; nucleophilic displacement; chlorination heterocycle; pyrimidine; nucleophilic displacement; chlorination
MDPI and ACS Style

Kalogirou, A.S.; Koutentis, P.A. Synthesis of 2-Cyanopyrimidines. Molbank 2019, 2019, M1086.

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