Cesium carbonate → HCID 11190126, compound

Participants

Reaction Steps

A solution of 3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (100 mg, 0.36 mmol) in DMF (1.8 mL) was charged with Cs2CO3 (174 mg, 0.54 mmol) and stirred at rt for 30 min. A solution of 2-bromobenzyl bromide (89.2 mg, 0.36 mmol) in DMF was added to the reaction mixture. Reaction mixture was stirred overnight at rt under nitrogen. The crude product was left under high vacuum to remove the DMF for 2 h. The product was then purified by silica gel column chromatography (3% NH3 in MeOH):CH2Cl2 to yield the title compound as a brown/red solid; 1H NMR (CDCl3, 400 MHz) δ 2.02-2.08 (m, 1H), 2.14-2.21 (m, 1H), 2.45-2.53 (m, 2H), 2.59-2.69 (m, 2H), 3.77-3.85 (m, 1H), 5.21 (s, 2H), 7.00 (d, J=5.6 Hz, 1H), 7.04-7.07 (m, 1H), 7.11 (d, J=5.2 Hz, 1H), 7.18-7.23 (m, 1H), 7.25-7.30 (m, 2H), 7.33-7.37 (m, 1H), 7.42 (t, J=16 Hz, 1H), 7.55-7.61 (m, 2H); MS (ES+): m/z 450.81 (100) [MH+].

Provenance & Evidence