The scope and limitations of using palladium-catalyzed cross-coupling reactions of diverse butyl metal species with two different 2-halopurines were evaluated. While tributylboranes reacted readily and regioselectively with both 2-chloro-6-dibenzylaminopurines and 2-iodo-6-chloropurines, all the other alkyl metal species were much less reactive and gave very poor yield and/or selectivity of the desired product. This protocol was applied to the synthesis of an important adenosine A2A receptor antagonist, ST1535.

Direct B-alkyl Suzuki-Miyaura cross-coupling of 2-halopurines. Practical synthesis os ST1535, a potent adenosine A2A receptor antagonist

BARTOCCINI, FRANCESCA;PIERSANTI, GIOVANNI;
2010

Abstract

The scope and limitations of using palladium-catalyzed cross-coupling reactions of diverse butyl metal species with two different 2-halopurines were evaluated. While tributylboranes reacted readily and regioselectively with both 2-chloro-6-dibenzylaminopurines and 2-iodo-6-chloropurines, all the other alkyl metal species were much less reactive and gave very poor yield and/or selectivity of the desired product. This protocol was applied to the synthesis of an important adenosine A2A receptor antagonist, ST1535.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2504286
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