Synthesis of Pyrimidine and Purine Bases. II

Bibliographic Information

Other Title
  • ピリミジンおよびプリン塩基の合成 (第2報)
  • マロン酸エステルからアデニンの合成 その2
  • Synthesis of Adenine from Malonic Ester. (2)

Abstract

Several efforts were made on the simplification of the steps, the attainment of higher yields, and the reduction of material costs in the synthesis of adenine from malonic ester reported in a previous paper.<br>(1) 4, 6-pyrimidinediol has been prepared in 80% yield from diethyl malonate and formamide by a one-step synthesis using ethanolic sodium ethoxide.<br>(2) Nitration of 4, 6-pyrimidinediol could be carried out in 95% yield with a mixture of nitric acid and sulfuric acid.<br>(3) Methanol could be used instead of ethanol as a solvent for amination of 4, 6-dichloro-5-nitropyrimidine to 4, 6-diamino-5-nitropyrimidine.<br>With these improvements, adenine has been prepared in 35% over-all yield from diethyl malonate by a five-step synthesis.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 85 (4), 367-370, 1965

    The Pharmaceutical Society of Japan

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