1234319-81-3Relevant articles and documents
Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 °c
Bosch, Lluís,Cial?cu, Ionela,Caner, Joaquim,Ariza, Xavier,Costa, Anna M.,Terrazas, Montserrat,Vilarrasa, Jaume
, p. 1358 - 1362 (2012/04/10)
Pd-catalysed reactions of 2-Cl, 2-Br and 2-I derivatives of a 6-chloropurine nucleoside with benzamide have been compared, using Pd 2dba3, Xantphos and Cs2CO3 in toluene, between 20 and 80 °C. The reactivity order was 2-I > 2-Br > 6-Cl ? 2-Cl. The 2-I substituent could be replaced even at 0 °C, under conditions disclosed here for the first time. On the other hand, the replacement of the chlorine atom at position 2 (2-Cl) required 110 °C.
15N double-labeled guanosine from inosine through ring-opening-ring-closing and one-pot Pd-catalyzed C-O and C-N cross-coupling reactions
Caner, Joaquim,Vilarrasa, Jaume
supporting information; experimental part, p. 4880 - 4883 (2010/10/19)
(Figure Presented) [N,1-15N2]-Guanosine, or [1,NH2-15N2]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with 15NH2OH, followed by conversion of the 15N-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and PhCO15NH2 or iPrCO15NH2 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.
