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Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
Shcherbakov, Stanislav S. Magometov, Artyom Yu. Shcherbakova, Viktoriia Yu. Aksenov, Alexander V. Domenyuk, Dmitriy A. Zelensky, Vladimir A. Rubin, Michael
Shcherbakov, Stanislav S.
Magometov, Artyom Yu.
Shcherbakova, Viktoriia Yu.
Aksenov, Alexander V.
Domenyuk, Dmitriy A.
Zelensky, Vladimir A.
Rubin, Michael
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Abstract
A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy.
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2020-03-10
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Royal Society of Chemistry
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Shcherbakov, S.S.; et al. Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines. RSC Adv., 2020,10, 10315-10321. https://doi.org/10.1039/D0RA01335H