HCID 18332609, compound → HCID 18332638, compound

Participants

Reaction Steps

To a solution of 2-[(1-benzyloxycarbonyl-piperidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (100 mg, 0.226 mmol, 1 eq) in THF (5 mL) ws added 10% Pd on carbon (24 mg). The flask was purged with hydrogen and the mixture was stirred under a balloon of hydrogen. After 1 h, no reaction was observed by thin layer chromatography analysis. Added 12 mg of Pd(OH)2 and let stir overnight under hydrogen. Still very little reaction by thin layer chromatography analysis. Filtered off catalyst and washed with THF and MeOH. Concentrated under reduced pressure. Dissolved the residue in MeOH (5 mL) and added Pd(OH)2 (24 mg). Purged flask with H2 and stirred under a balloon of H2 for several hours. Purged the vessel with nitrogen and filtered off and washed the catalyst with methanol. Concentrated the mixture under reduced pressure and purified by silica gel chromatography (eluted with 3.5% MeOH/CH2Cl2 then 7% (2N NH3 in MeOH)/CH2Cl2) to give 53.2 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 1.2-1.3 (1H, m), 1.4-1.5 (1H, m), 1.55-1.95 (3H, m), 2.61 (1H, dd, J=10 Hz, J=11.5 Hz), 2.62 (1H, dd, J=2.5 Hz, J=12 Hz), 3.03 (1H, d, J=12 Hz), 3.19 (1H, d, J=11.5 Hz), 3.4-3.45(2H, m), 5.5 (1H br s), 6.8 (1H, d, 5.5 Hz), 7.40-7.45 (2H, m), 7.87 (1H, d, J=8.5 Hz), 8.20 (1H br d), 8.39 (1H, br s), 8.64 (1H, s). Mass spectrum (ESI) 309.1 (M+1).

Provenance & Evidence