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 A(2A) receptor antagonist, ST1535.
Bartoccini F, Cabri W, Celona D, Minetti P, Piersanti G, Tarzia G (2010). Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of 2-Halopurines. Practical Synthesis of ST1535, a Potent Adenosine A(2A) Receptor Antagonist. JOURNAL OF ORGANIC CHEMISTRY, 75(15), 5398-5401 [10.1021/jo101027h].
Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of 2-Halopurines. Practical Synthesis of ST1535, a Potent Adenosine A(2A) Receptor Antagonist
Cabri W;
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 A(2A) receptor antagonist, ST1535.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
