Methanol → 2-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-2-(7H-purin-6-ylamino)-ethanol

Participants

Reaction Steps

To a solution of [(R)-2-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-(7H-purin-6-yl)amine (124 mg, 0.26 mmol) in anhydrous DCM (3 mL) at 0° C. under a nitrogen atmosphere was added boron tribromide (1.0M in DCM, 0.3 mL, 0.26 mmol) dropwise. The reaction mixture was slowly warmed to RT and stirred at RT for 1 h. Additional BBr3 (0.3 mL) was added and stirring continued for 1 h. MeOH was added then the volatiles removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 172 (60 mg, 59%). LCMS (Method K): RT 3.11 min [M+H]+ 390.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.93 (0.8H, s), 12.17 (0.2H, s), 8.27-8.01 (2H, m), 7.74-7.43 (6H, m), 7.16-7.01 (1H, m), 6.93-6.79 (1H, m), 5.56-5.31 (1H, m), 5.21-5.02 (1H, m), 3.95-3.74 (2H, m). Signals split due to presence of rotamers/tautomers

Provenance & Evidence