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Improved and Scalable Preparation of 6-Bromo-4-Chlorothieno[2,3-d]Pyrimidine

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Chemistry of Heterocyclic Compounds Aims and scope

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 to obtain the product in an overall yield of 49% without using chromatography for purification of the product and intermediates.

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Notes

  1. * As an exception, scale in this case is based on amount of product produced in the reaction. If nothing else is indicated, scale is based on the amount of substrate for the reaction.

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Authors and Affiliations

  1. Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, Trondheim, NO-7491, Norway

    S. Bugge, E. M. Skjønsfjell, F. B. Willumsen & B. H. Hoff

  2. Sør-Trøndelag University College, E. C. Dahls Gate 2, Trondheim, NO-7004, Norway

    E. Sundby

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  1. S. Bugge
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  2. E. M. Skjønsfjell
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  3. F. B. Willumsen
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  4. E. Sundby
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  5. B. H. Hoff
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Correspondence to B. H. Hoff.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1275-1285, August, 2014.

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Bugge, S., Skjønsfjell, E.M., Willumsen, F.B. et al. Improved and Scalable Preparation of 6-Bromo-4-Chlorothieno[2,3-d]Pyrimidine. Chem Heterocycl Comp 50, 1177–1187 (2014). https://doi.org/10.1007/s10593-014-1579-z

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  • DOI: https://doi.org/10.1007/s10593-014-1579-z

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