Benzylamine → Diisopropylethylamine

Participants

Reaction Steps

For the synthesis of the 6-benzylamino-, 6-(pyridin-2-ylmethyl), 6-(pyridin-3-ylmethyl) and 6-(pyridin-2-ylmethyl)-intermediates, the initial step involved reaction of 6-chloro-2-fluoro-purine 29 [Gray, N. S.; Kwon, S.; Schultz, P. G. Tetrahedron Lett., 1997, 38 (7), 1161-1164] with either benzylamine, 2-(aminomethyl)pyridine, 3-(aminomethyl)pyridine or 4-(aminomethyl)pyridine, in n-BuOH the presence of DIPEA, to afford the corresponding 6-substituted intermediates 30. These compounds then underwent reaction with 2-bromopropane and K2CO3 in DMA [Havlicek, L.; Hunus, J.; Vesely, J.; Leclerc, S.; Meijer; L.; Shaw, G.; Strnad, M.; J Med Chem., 1997, 40 (4), 408412], to afford their corresponding N9-isopropyl substituted intermediates 31. These purine intermediates were finally reacted with the aminoalcohols (1-2, 15-22, and 27-28) in DMSO/n-BuOH/DIEA at 140° C. over 72 h to give their corresponding C2-substituted aminoalkyl analogues 32.

Provenance & Evidence