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A one-step, atom economical synthesis of thieno[2,3-d]pyrimidin-4-amine derivatives via a four-component reaction.

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.

SUBMITTER: Shi T

PROVIDER: S-EPMC6922009 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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A one-step, atom economical synthesis of thieno[2,3-d]pyrimidin-4-amine derivatives via a four-component reaction.

Shi Taoda T Zerio Christopher J CJ Sivinski Jared J Ambrose Andrew J AJ Moore Kohlson T KT Buckley Thomas T Kaneko Lynn L Zhang Mae M Zhang Donna D DD Chapman Eli E

European journal of organic chemistry 20190430 2

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. ...[more]

PMID: 31857792

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