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Open AccessFeature PaperCommunication

Synthesis of 2-Cyanopyrimidines

1
Department of Life Sciences, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus
2
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; https://doi.org/10.3390/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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