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A One‐Step, Atom Economical Synthesis of Thieno[2,3‐ d ]pyrimidin‐4‐amine Derivatives by a Four‐Component Reaction
Author(s) -
Shi Taoda,
Zerio ChristopherJ.,
Sivinski Jared,
Ambrose Andrew J.,
Moore Kohlson T.,
Buckley Thomas,
Kaneko Lynn,
Zhang Mae,
Zhang Donna D.,
Chapman Eli
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900414
Subject(s) - chemistry , malononitrile , ketone , amine gas treating , atom economy , component (thermodynamics) , formamide , combinatorial chemistry , medicinal chemistry , catalysis , reaction conditions , organic chemistry , physics , thermodynamics
A Na 2 HPO 4 ‐catalyzed four‐component reaction between a ketone, malononitrile, S 8 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.