A One-Step, Atom Economical Synthesis of Thieno[2,3-d]pyrimidin-4-amine Derivatives by a Four-Component Reaction

Taoda Shi, Christopher J. Zerio, Jared Sivinski, Andrew J. Ambrose, Kohlson T. Moore, Thomas Buckley, Lynn Kaneko, Mae Zhang, Donna D. Zhang, Eli Chapman

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

A Na2HPO4-catalyzed four-component reaction between a ketone, malononitrile, S8 and formamide has been realized for the first time. This reaction provides a concise approach to thieno[2,3-d]pyrimidin-4-amines, previously requiring 5 steps. The utility of this reaction was validated by preparing a multi-targeted kinase inhibitor and an inhibitor of the NRF2 pathway with excellent atom- and step-economy.

Original languageEnglish (US)
Pages (from-to)3269-3272
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number20
DOIs
StatePublished - Jun 2 2019

Keywords

  • Atom economy
  • Multi-component reaction
  • Organocatalysis
  • Structural diversity
  • Thieno[2,3-d]pyrimidin-4-amines

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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