Stannous chloride dihydrate → HCID 86675703, compound

Participants

Reaction Steps

To a solution of 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (21.76 g, 89.54 mmol) in acetic acid (108.8 mL) and concentrated hydrogen chloride (108.8 mL) was added dichlorotin dihydrate (101.0 g, 447.7 mmol). The reaction mixture was left to stir for 1 hour at ambient temperature. Reaction mixture was quenched by addition of 2M NaOH solution and the aqueous extracted with EtOAc (×3). Organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting solid was washed with saturated NaHCO3 solution and the solid collected, washed with water and dried to give 2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-amine (10.4 g, 54.6%). 1H NMR (400.0 MHz, DMSO) δ 11.50 (br s, 1H), 8.22 (s, 1H), 7.16 (s, 1H) and 4.35 (br s, 2H) ppm; MS (ES+) 214.79

Provenance & Evidence