Boron tribromide → HCID 178461938, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [(S)-1-[1-(3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]-(9H-purin-6-yl)amine (0.13 g, 0.29 mmol) in DCM (5 mL) was cooled to 0° C. To this mixture was added boron tribromide (2.1 mL, 1.43 mmol) dropwise and the resultant mixture stirred at RT for 2 h. The reaction mixture was quenched with MeOH (2 mL) and concentrated in vacuo. The resulting yellow solid was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 390 as an off-white glassy solid (50 mg, 50%). 1H NMR (DMSO-d6): δ 8.98 (1H, s), 8.55-8.37 (2H, m), 7.93 (1H, d, J=9.74 Hz), 7.69 (1H, dd, J=8.92, 4.99 Hz), 7.21 (1H, t, J=9.90 Hz), 5.89 (1H, s), 4.86-4.75 (1H, m), 4.05-3.95 (1H, m), 2.97-2.62 (4H, m), 1.70 (3H, d, J=6.75 Hz)

Provenance & Evidence