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

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journal contribution
posted on 03.02.2020, 11:43 authored by Shuya Yamada, Kaylin Nicole Flesch, Kei Murakami, Kenichiro Itami
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.