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Synthesis 1987; 1987(6): 579-581
DOI: 10.1055/s-1987-28013
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A New Route to 5,6-Dihydropyrimidin-4(3H)-ones

Lucjan Strekowski* , Rebecca A. Watson, Michelle A. Faunce
  • *Department of Chemistry, Georgia State University, Atlanta, GA 30303, U.S.A.
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Publication Date:
20 August 2002 (online)

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The addition reaction of 2,4-bis(methylthio)pyrimidine or 2, 4-dimethoxypyrimidine with organolithium reagents produces unstable 6-substituted 2,4-bis(methylthio)-5,6-dihydropyrimidines and 2, 4-dimethoxy-5,6-dihydropyrimidines, respectively. The regioselective hydrolysis of these addition products gives the respective 6-substituted 2-methylthio-5,6-dihydropyrimidin-4(3H)ones and 6-substituted 2-methoxy-5,6-dihydropyrimidin-4(3H)ones. The methoxy products can be hydrolyzed further to 6-substituted dihydrouracils.