A One‐Step, Atom Economical Synthesis of Thieno[2, 3‐d]pyrimidin‐4‐amine Derivatives by a Four‐Component Reaction. Issue 20 (20th May 2019)

• Record Type: Journal Article
• Authors: Shi, Taoda; Zerio, ChristopherJ.; Sivinski, Jared; Ambrose, Andrew J.; Moore, Kohlson T.; Buckley, Thomas; Kaneko, Lynn; Zhang, Mae; Zhang, Donna D.; Chapman, Eli
• Is Part Of: European journal of organic chemistry. Issue 20(2019)
• Page Start: 3269
• Page End: 3272
• Publication Date: 2019-05-20
• Subjects: Atom economy -- Multi‐component reaction -- Organocatalysis -- Thieno[2, 3‐d]pyrimidin‐4‐amines -- Structural diversity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900414
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A Na2 HPO4 ‐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. Abstract : Concise synthesis of thieno[2, 3‐ d ]pyrimidin‐4‐amines with improved atom economy, increased step economy, enhanced structural diversity, and simplified purification has been realized.