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Synthesis 1990; 1990(3): 243-245
DOI: 10.1055/s-1990-26843
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Synthesis of 2,4-Dimethoxy-5-(3-oxo-1-alkynyl)pyrimidines, 2,4-Dimethoxy-5-(3-oxoalkyl)pyrimidines, and 5-(3-Oxoalkyl)uracils by a Highly Convenient Procedure

Nitya G. Kundu* , Biswajit Das, Anjali Majumdar
  • *Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadhavpur, Calcutta - 700 032, India
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Publication Date:
17 September 2002 (online)

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A simple synthesis of 2,4-dimethoxy-5-(3-oxoalkynyl)pyrimidines from the readily available 5-ethynyl-2,4-dimethoxypyrimidine is described. The sequence proceeds via an ethynylboron intermediate which is acylated with carboxylic anhydrides. The 5-(3-oxo-1-alkynyl) products are hydrogenated to the saturated analogs and these are O-dealkylated with chlorotrimethylsilane/sodium iodide to give 5-(3-oxoalkyl)uracils, e.g., 5-(3-oxobutyl)-, 5-(3-oxopentyl)-, and 5-(3-oxohexyl)uracil. These compounds and the nucleosides derived therefrom are of interest as anticancer and antiviral agents.