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Synthesis 1989; 1989(4): 316-317
DOI: 10.1055/s-1989-27240
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A Convenient Synthesis of 7-Aryl-2,4-dimethoxy-5-oxo-5H-pyrano[4,3-d]pyrimidines

Akimori Wada* , Takeshi Nakagawa, Shōichi Kanatomo
  • *School of Pharmacy, Hokuriku University, Ho-3, Kanagawamachi, Kanazawa 920-11, Japan
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Publication Date:
17 September 2002 (online)

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A convenient synthesis of 7-aryl-2,4-dimethoxy-5-oxo-5H-pyrano[4,3-d]pyrimidines 6 is described. The lithium salt of methyl 2,4-dimethoxy-6-methyl-5-pyrimidinecarboxylate (2) reacts smoothly with aromatic aldehydes to afford cycloaddition products 4 in good yields. When 4 is treated with N-bromosuccinimide, aromatization occurs to give 5-oxo-5H-pyrano[4,3-d]pyrimidines 6 via dehydrobromination from the 8-bromo derivatives 5 in satisfactory yields.