IMPROVED AND SCALABLE PREPARATION OF 6-BROMO-4-CHLOROTHIENO[2,3-<i>d</i>]PYRIMIDINE

Authors

  • S. Bugge Norwegian University of Science and Technology, Department of Chemistry
  • E. M. Skjønsfjell Norwegian University of Science and Technology, Department of Chemistry
  • F. B. Willumsen Norwegian University of Science and Technology, Department of Chemistry
  • E. Sundby Trondheim University Collage (HIST)
  • B. H. Hoff Norwegian University of Science and Technology, Department of Chemistry

DOI:

https://doi.org/10.1007/1824

Keywords:

6-bromo-4-chlorothieno[2, 3-d]pyrimidine, thienopyrimidine, Design of Experiments (DoE), Gewald reaction, scale-up

Abstract

A practical, robust and scalable synthesis of 6-bromo-4-chlorothieno[2,3-d]pyrimidine starting from cheap bulk chemicals has been developed. The method involves four synthetic steps: Gewald reaction, pyrimidone formation, bromination, and chlorination. The process relies on standard laboratory equipment, allowing for obtaining the product in an overall yield of 49% without using chromatography for purification of the product and intermediates.

How to Cite
Bugge, S.; Skjønsfjell, E. M.; Willumsen, F. B.; Sundby, E.; Hoff, B. H. Chem. Heterocycl. Compd. 2014, 50, 1177. [Khim. Geterotsikl. Soedin. 2014, 1275.]

For this article in the English edition see DOI 10.1007/s10593-014-1579-z

Author Biographies

S. Bugge, Norwegian University of Science and Technology, Department of Chemistry

Steffen Bugge

E. M. Skjønsfjell, Norwegian University of Science and Technology, Department of Chemistry

Ellen Martine Skjønsfjell

F. B. Willumsen, Norwegian University of Science and Technology, Department of Chemistry

Fredrik Bysting Willumsen

E. Sundby, Trondheim University Collage (HIST)

Eirik Sundby

B. H. Hoff, Norwegian University of Science and Technology, Department of Chemistry

Bård Helge Hoff

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Published

2014-09-09

Issue

No. 8 (2014)

Section

Original Papers