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Communication | Regular issue | Vol 16, No. 3, 1981, pp.387-390
Published online, 1st January, 1970
DOI: 10.3987/R-1981-03-0387
Pyrimidinylcyclopropanes. Synthesis and Reactions

Tetsuzo Kato,* Nobuya Katagiri, Akihiro Wagai, and Yumiko Katagiri

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Reactions of trichloromethylpyrimidines (1 - 4) with dimethyl fumarate in the presence of t-butyl isocyanide and copper powder in benzene gave the corresponding dimethyl 3-chloro-3-(4- or 6-pyrimidinyl)cyclopropane-1,2-trans-dicarboxylates (5 - 8). Similar reactions with methyl vinyl ketone afforded the corresponding 2-acetyl-1-chloro-1-(4- or 6-pyrimidinyl)cyclopropanes (9 - 12). Pyrimidinylcyclopropanes (10 and 12), on treatment with sodium ethoxide, underwent ring opening of cyclopropane to give 1-pyrimidinyl-4-oxopentanes (13 - 16).