Chloroacetone → 2,6-Dimethylimidazo[1,2-b]pyridazine

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Reaction Steps

A solution of 3-amino-6-methyl-pyridazine (4.53 g, 41.58 mmol) in EtOH (60 mL) is treated with chloroacetone (3.5 mL, 43.66 mmol). The reaction is refluxed overnight. While it is hot, NaHCO3 (8.7 g, 103.9 mmol) is added in portions. The resulting mixture is refluxed for 2 h. It is cooled to rt and filtered through silical gel, washed with EtOAc, and concentrated. Purification of the crude material by chromatography gives the title compound (3.1 g, 21.11 mmol, 51%). 1H NMR (CDCl3): δ 2.49 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=9.3 Hz, 1H), 7.64 (s, 1H), 7.70 (d, J=9.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C8H9N3 (M+H)+: 148.2. found: 148.1.

Provenance & Evidence