Methanol → HCID 178520771, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [(S)-3-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]-(9H-purin-6-yl)amine (296 mg, 0.6 mmol) in anhydrous DCM (6 mL) at 0° C. under a nitrogen atmosphere was added dropwise boron tribromide (1.0 M in DCM, 1.2 mL, 1.2 mmol). The reaction mixture was stirred at 0° C. for 1 h. MeOH was then added and the volatiles were removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 187 (160 mg, 66%). LCMS (Method K): RT 3.10 min [M+H]+ 404.1 1H NMR (DMSO-d6, 400 MHz): δ 12.55 (1H, s), 8.28-7.83 (3H, m), 7.81-7.44 (6H, m), 7.16-7.01 (1 m), 6.91-6.79 (1H, m), 5.56 (1H, br s), 4.60 (1H, br s), 3.57-3.38 (2H, m), 2.23-2.00 (2H, m). Signals split due to presence of rotamers/tautomers

Provenance & Evidence