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Abstract
The synthesis and modification of 2′-deoxyuridine has been realized under Suzuki-Miyaura palladium-catalyzed cross-coupling conditions. Using Pd(PPh 3 ) 4 and Na 2 CO 3 , 5-iodo-2′-deoxyuridine bound to solid support is coupled with various boronic acids to give 5-(hetero)aryl-2′-deoxyuridine. Pd(PPh 3 ) 4 palladium catalyzed was found to be superior to Pd(OAc) 2 and (NHC)Pd(allyl)Cl for Suzuki-Miyaura palladium-catalyzed reactions.
Notes
a Conversions were calculated from 1H MNR of crude product after cleavage.
b Yields (after 5 steps).