Dimethylformamide → 8-Chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Participants

Reaction Steps

A solution of formamide N-[(3-chloro-pyrazin-2-yl)-(4-phenoxy-phenyl)-methyl]-formamide (1.85 g, 5.45 mmol) in CH3CN (50 mL) at 0° C. was added DMF (0.4 mL) and POCl3 (1.52 mL, 16.3 mmol). The mixture was allowed to warm to rt over 16 h. TLC (EtOAc/CH2Cl2, 1:1) showed no starting material. Reaction mixture was evaporated to remove solvents. To the residue was added aq. satd. NaHCO3 (100 mL) and extracted with EtOAc (3×50 mL). Organic layer was washed with water (30 mL) and dried (Na2SO4). Evaporation of solvent gave titled compound (1.62 g, 92%). 1H NMR (CDCl3, 300 MHz) δ 7.13-7.21 (m, 5H), 7.29-7.31 (m, 3H), 7.60-7.64 (m, 2H), 7.68 (d, J=2.4 Hz, 1H), 8.30 (s, 1H).

Provenance & Evidence