NEW METHOD FOR THE SYNTHESIS OF THIENO[2,3-<i>d</i>]PYRIMIDINES

Authors

  • O. B. Ryabova State Antibiotics Research Center, 117105 Moscow
  • M. I. Evstratova State Antibiotics Research Center, 117105 Moscow
  • V. A. Makarov State Antibiotics Research Center, 117105 Moscow
  • V. A. Tafeenko M. V. Lomonosov Moscow State University, 119234 Moscow
  • V. G. Granik State Antibiotics Research Center, 117105 Moscow

DOI:

https://doi.org/10.1007/s10593-005-0082-y

Keywords:

isothiazolo[5,4-d]pyrimidine, nitromethane, thieno[2,3-d]pyrimidine, 5-formylpyrimidine

Abstract

The reaction of 5-formyl-4-thiocyanatopyrimidines with nitromethane was studied under various conditions. The reaction was found unexpectedly to proceed with closure of a thiophene ring to give thieno[2,3-d]pyrimidines. The use of ammonium acetate as the catalyst leads to a side reaction involving closure of an isothiazole ring to give isothiazolo[5,4-d]pyrimidines. X-ray diffraction crystallographic analysis was used to confirm the structure of thieno[2,3-d]pyrimidine.

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Published

2004-10-25

Issue

No. 10 (2004)

Section

Original Papers