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Synlett 1999; 1999(6): 756-758
DOI: 10.1055/s-1999-2741
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One-pot Preparation of 2,6-Disubstituted 4-(Trifluoromethyl)pyrimidines via the Tandem Cyclization, Dehydration, and Oxidation Reaction of α,β-Unsaturated Trifluoromethyl Ketones Using POCl3-Pyridine-Silica Gel and MnO2 Systems

Kazumasa Funabiki* , Hiroko Nakamura, Masaki Matsui, Katsuyoshi Shibata
  • *Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu, 501-1193, Japan; Fax +81-58-2 30-18 93; E-mail: kfunabik@apchem.gifu-u.ac.jp
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Publication Date:
31 December 1999 (online)

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The treatment of α,β-unsaturated trifluoromethyl ketones with amidines in acetonitrile gave the corresponding 4-hydroxy-4-(trifluoromethyl)-3,5,6-trihydropyrimidines, followed by successive dehydration with phosphorus oxychloride-pyridine-silica gel and oxidation with manganese(IV) oxide, producing 2,6-disubstituted 4-(trifluoromethyl)pyrimidines in good to excellent yields.

4-(trifluoromethyl)pyrimidine - POCl3-pyridine - silica gel - dehydration - oxidation