Synthesis of Pyrimidine and Purine Bases. I

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Bibliographic Information

Other Title
  • ピリミジンおよびプリン塩基の合成 (第1報)
  • マロン酸エステルからアデニンの合成 その1
  • Synthesis of Adenine from Malonic Ester. (1)

Abstract

The new process for synthesis of adenine from malonic ester has been investigated. Adenine has been prepared in 25% over-all yield from diethyl malonate by a six-step synthesis which involves: (1) reaction of diethyl malonate with conc. ammonium hydroxide solution to give malonamide (76%), (2) condensation of the amide with formamide in ethanolic sodium ethoxide to give 4, 6-pyrimidinediol (76%), (3) nitration of 4, 6-pyrimidinediol in glacial acetic acid with fuming nitric acid to give 5-nitro-4, 6-pyrimidinediol (95%), (4) chlorination of 5-nitro-4, 6-pyrimidinediol with phosphorus oxychloride and N, N-dimethylaniline as a basic catalyst to give 4, 6-dichloro-5-nitropyrimidine (71%), (5) amination of 4, 6-dichloro-5-nitropyrimidine with alcoholic ammonia to give 4, 6-diamino-5-nitropyrimidine (98%) and (6) heating 4, 6-diamino-5-nitropyrimidine with formamide, formic acid and sodium dithionite to give adenine (67%).

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 85 (4), 364-367, 1965

    The Pharmaceutical Society of Japan

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