A. V. Erkin, V. Krutikov
2004
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Journal
Russian Journal of General Chemistry
Abstract
Oxopyrimidine-5-carbaldehydes I and some of their derivatives (azomethines, hydrazones) show promise as synthetic precursors of antitumor agents [1, 2]. Aldehydes I are usually synthesized by the Reimer Tiemann reaction [3], controlled oxidation of 5-hydroxymethylpyrimidines [4], or Vilsmeier reaction. The latter reaction can be accompanied by exchange chlorination of oxo groups of the pyrimidine ring. For example, heating of 6-aminouracil II with POCl3 in DMF yields 6-amino-2,4-dichloro-5-formylpyrimidine [5]. At the same time, there are indications in the literature [6] that Vilsmeier formylation of amine II can be performed so as to leave the oxo groups intact.