Synthetic Studies on an Antitumor Antibiotic, Bleomycin. XIII. Synthesis of 2-Formylpyrimidine, a Key Intermediate for the Pyrimidine Moiety of Bleomycin

MASAMI OTSUKA; SUSUMU KOBAYASHI; MASAJI OHNO; YOJI UMEZAWA; HAJIME MORISHIMA; HAMAO UMEZAWA

doi:10.1248/cpb.33.515

MASAMI OTSUKA, SUSUMU KOBAYASHI, MASAJI OHNO, YOJI UMEZAWA, HAJIME MORISHIMA, HAMAO UMEZAWA

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Keywords: formylpyrimidine

JOURNAL FREE ACCESS

1985 Volume 33 Issue 2 Pages 515-519

DOI https://doi.org/10.1248/cpb.33.515

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Abstract

An efficient synthesis of the pyrimidine nucleus of bleomycin was achieved. The reaction of diethoxyacetamidine and ethyl ethoxalylpropionate gave ethyl 2-diethoxymethyl-6-hydroxy-5-methylpyrimidine-4-carboxylate in 76% yield ; this product was then converted into ethyl 6-chloro-2-formyl-5-methylpyrimidine-4-carboxylate in 85% yield by treatment with POCl₃.

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