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Communication | Regular issue | Vol 38, No. 2, 1994, pp.249-252
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6569
Novel Synthesis of Substituted Pyrimidines: A Ring Transformation of 3-Methyl-5-nitropyrimidin-4(3H)-one

Nagatoshi Nishiwaki, Tomoko Matsunaga, Yasuo Tohda, and Masahiro Ariga*

*Department of Chemistry, Osaka Kyoiku University, 4-698-1 Asahigaoka, Kashiwara, Osaka 582-8582, Japan


A novel ring transformation of 3-methyl-5-nitropyrimidin-4(3H)-one with ketones in the presence of ammonia was found to be an elegant method for synthesizing 5,6-disubstituted pyrimidines. Tetrahydroquinazoline was readily obtained in good yields when cyclohexanone was employed as a substrate. The present reaction was applicable to cyclopentanone, acetophenone and p-nitroacetophenone to give the corresponding pyrimidine derivatives.