Ammonia → HCID 16755042, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-benzyloxy-phenyl)-8-chloro-2H-imidazo[1,5-a]pyrazin-3-one (100 mg, 0.28 mmol) in i-PrOH (4 mL) was saturated with NH3 at −20° C. and heated 110° C. in a sealed tube for 48 hours. The light brown reaction mixture was partitioned in water and DCM and separated. The aqueous layer was washed with DCM (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by chromatography on silica gel [eluting with 8% MeOH in DCM], resulting in the title compound as a pale brown solid; 1H NMR (DMSO-d6, 400 MHz) δ=5.16 (s, 2H), 5.86 (brs, 2H), 6.70 (d, J=5.2 Hz, 1H), 7.01 (d, J=4.8 Hz, 1H), 7.07-7.14 (m, 2H), 7.24 (brt, J=2 Hz, 1H), 7.32-7.49 (m, 7H); MS (ES+): m/z=333.21 (100) [MH+], HPLC: tR=2.05 min (MicromassZQ, polar—5 min).

Provenance & Evidence