Cesium carbonate → HCID 67417834, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(8-amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (28 mg, 0.1 mmol) in anhydrous DMF (1 ml) was added cesium carbonate (49 mg, 0.15 mmol) followed by a solution of 2-bromoethanol (12.5 mg, 0.1 mmol) in DMF (0.5 ml). The reaction was stirred at 60° C. overnight. The reaction was poured onto saturated NaHCO3 (10 ml) and extracted with EtOAc (2×10 ml). The combined organics were washed with water (10 ml) and aqueous brine solution (3×10 ml), dried (MgSO4), filtered and concentrated in vacuo. Purification by mass-directed HPLC gave 2-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxy]-ethanol formic acid salt (4.0 mg, 12%) as an off-white solid: 1H NMR (400 MHz, CD3OD) δ 8.54 (s, 1H), 7.48-7.41 (m, 2H), 7.13-7.09 (m, 2H), 7.01 (d, 1H, J=10.3 Hz), 6.93 (d, 1H, J=5.8 Hz), 4.14 (t, 2H, J=4.9 Hz), 4.03-3.97 (m, 1H), 3.92 (t, 2H, J=4.9 Hz), 2.61-2.51 (m, 4H), 2.15-2.10 (m, 1H), 2.06-2.01 (m, 1H), 3H not observed (NH2 & OH); LCMS (ES+) m/z 325.08 [MH+] at Rt 2.39 min.

Provenance & Evidence