Dimethylformamide → 2-Amino-6-chloroimidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

To a 100-mL, round-bottomed flask was added azido(6-chloroimidazo[1,2-b]pyridazin-2-yl)methanone from Step 2 (2.3 g, 10 mmol) and DMF (40 mL). The solution was heated to 100° C. and H2O (1.8 mL, 100 mmol) was added. The mixture was stirred for 45 min and then allowed to cool to room temperature. The mixture was poured into water (150 mL) and then concentrated in vacuo. The solid residue was dissolved in 1:2 MeOH/CH2Cl2 (900 mL) and concentrated onto silica. Purification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a yellow-green solid (0.71 g, 42% yield). MS (ESI positive ion) m/z: 169 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 7.69 (d, J=9.2 Hz, 1H), 7.37 (s, 1H), 7.05 (d, J=9.2 Hz, 1H), 5.74 (broad s, 2H).

Provenance & Evidence