Synthesis of thieno[2,3-d]pyrimidine analogues from a thiophene moiety

  • Ravi Teja B Institute of Pharmacy, C. S. J. M. University, Kanpur, Uttar Pradesh-208024
  • Sreelakshmi M Pharmaceutical Chemistry Department, MAM College of Pharmacy, Narasaraopet, Andhra Pradesh, India-522601
  • Ajay Kumar G Institute of Pharmacy, C. S. J. M. University, Kanpur, Uttar Pradesh-208024
  • Pratima K Institute of Pharmacy, C. S. J. M. University, Kanpur, Uttar Pradesh-208024

Abstract

Four novel thieno[2,3-d]pyrimidine analogues, 6a-b and 7a-b were synthesized  by using 6-Bromo-2-chloro-thieno[2,3-d]pyrimidine (3), which was synthesized from commercially available thiophene derivative, 2-aminothiophene-3-carboxylate (1). Initially, pyrimidine framework was performed by strong heating of 1 in formamide and then by using Vilsmeier reagent, conversion of 4-oxo group of 2 into chlorine was achieved. By regioselectivity approach at position 6 of 3 with n-BuLi and CBr4 at low temperature gives 4a-b. Introduction of Suzuki coupling reactions on 4a-b with 4-fluorophenylboronic acid afforded the desired compounds 5a-b respectively. Finally, by using different reagents under mild and vigorous conditions, the position 4 of   5a-b, 6a-b and 7a-b were synthesized.

Keywords: Thieno[2,3-d]pyrimidine, 6-Bromo-2-chloro-thieno[2,3-d]pyrimidine, Vilsmeier reagent and Suzuki coupling.

References

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Teja B, R., M, S., Kumar G , A., & K, P. (2018). Synthesis of thieno[2,3-d]pyrimidine analogues from a thiophene moiety. Journal of Integral Sciences, 1(3), 6-11. Retrieved from https://jisciences.com/index.php/journal/article/view/16
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