Methanol → HCID 178520772, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [(S)-3-benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)propyl](7H-purin-6-yl)amine (465 mg, 0.8 mmol) in anhydrous DCM (8 mL) at 0° C. under a nitrogen atmosphere was added dropwise boron tribromide (1.0 M in DCM, 2.4 mL, 2.4 mmol). The reaction mixture was stirred at 0° C. for 1 h. MeOH was added and the volatiles removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-15% MeOH in DCM) to afford 304 as a white solid (143 mg, 44%). LCMS (Method K): RT 2.73 min [M+H]+ 404.9. 1H NMR (DMSO-d6, 400 MHz): δ 9.56-9.48 (1H, m), 8.65-8.57 (2H, m), 8.49 (1H, s), 8.11 (1H, td, J=7.74, 1.90 Hz), 7.83-7.74 (2H, m), 7.56 (1H, t, J=6.09 Hz), 7.28-7.16 (2H, m), 6.07-5.97 (1H, m), 3.59-3.45 (2H, m), 2.39-2.29 (1H, m), 2.24-2.12 (1H, m)

Provenance & Evidence