Rapid Access to Kinase Inhibitor Pharmacophores by Regioselective C–H Arylation of Thieno[2,3‑d]pyrimidine

Regioselective C–H arylations of thieno­[2,3-d]­pyrimidine are accomplished under palladium catalysis. Thieno­[2,3-d]­pyrimidines react with aryl iodides at the C6-position and with aryl boronic acids at the C5-position, showing excellent regioselectivity. Mechanistic investigations indicate that th...

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Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (4), p.1547-1551
Main Authors: Yamada, Shuya, Flesch, Kaylin Nicole, Murakami, Kei, Itami, Kenichiro
Format: Article
Language:English
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Summary:Regioselective C–H arylations of thieno­[2,3-d]­pyrimidine are accomplished under palladium catalysis. Thieno­[2,3-d]­pyrimidines react with aryl iodides at the C6-position and with aryl boronic acids at the C5-position, showing excellent regioselectivity. Mechanistic investigations indicate that the regioselectivity is controlled by the nature of the palladium catalyst: the cationic palladium favorably arylates the C5-position. The utility of this direct arylation has been highlighted in the streamlined synthesis of kinase inhibitors and their derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00143