Hydrogen Bromide → HCID 18332644, compound

Participants

Reaction Steps

To a 0° C. solution of 150 mg of 2-[(1-(benzyloxycarbonyl)-pyrrolidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (from EXAMPLE 11, step C) in 3 mL of CH2Cl2 was added 1 mL of 30% HBr in acetic acid. The cooling bath was removed after 5 min and the mixture was stirred at room temperature for 1 h, then diluted with 20 mL of water and extracted with 2×5 mL of CH2Cl2. The pH of the aqueous phase was adjusted to 11 with 5 N NaOH, and the aqueous phase was extracted with 5×10 mL of EtOAc, with continuous monitoring of the pH. The combined EtOAc extracts were dried over MgSO4 and concentrated to yield 40 mg of the title compound as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 8.62 (s, 1H), 8.38 (br s, 1H) 8.18 (d, J=7.6 Hz, 1H), 7.85 (dd, J=1.8, 7.1 Hz, 1H), 7.33-7.42 (m, 2H), 6.79 (d, J=5.5 Hz, 1H), 3.52 (t, J=6.4 Hz, 2H), 3.03-3.16 (m, 2H), 2.71-3.00 (m, 1H), 2.79 (dd, J=5.7, 11.0 Hz, 1H), 2.46-2.37 (m, 1H), 1.96-2.20 (m, 1H), 1.52-1.60 (m, 1H).

Provenance & Evidence