Cesium carbonate → HCID 67416502, compound

Participants

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 3-methoxybenzyl bromide (20 mg, 0.1 mmol) in DMF (0.5 ml). The reaction was stirred at room temperature 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, to give 3-cyclobutyl-1-[3-(3-methoxy-benzyloxy)-phenyl]-imidazo[1,5-a]pyrazin-8-ylamine as a brown solid (24.1 mg, 60%): 1H NMR (400 MHz, CDCl3) δ 7.42 (t, 1H, J=7.8 Hz), 7.35-7.27 (m, 3H), 7.13 (d, 1H, J=5.1 Hz), 7.08-7.03 (m, 4H), 6.90 (d, 1H, J=8.6 Hz), 5.17 (s, 2H), 3.84 (s, 3H), 3.86-3.79 (m, 1H, obscured), 2.72-2.62 (m, 2H), 2.56-2.47 (m, 2H), 2.25-2.14 (m, 1H), 2.11-2.02 (m, 1H), 2H not observed (NH2); LCMS (ES+) m/z 401.34 [MH+] at Rt 3.20 min.

Provenance & Evidence