Chloroacetone → 2,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-ylamine (850 mg, 4.74 mmol), chloroacetone (0.415 ml, 5.22 mL) and 20 mL of ethanol are heated in the microwave at 110° C. for 35 minutes. Sodium bicarbonate (1.2 g, 14.2 mmol) is added, and the reaction mixture is heated in an oil bath at 100° C. overnight. The solvent is evaporate and the residue is taken up in ethyl acetate and washed three times with brine. The organic layer is dried over sodium sulfate, filtered, and evaporated to a brown oil. The crude product is purified via silica gel chromatography using a hexane:ethyl acetate gradient. The title compound is an oil weighing 3.69 g (17.0 mmol, 84%). 1H-NMR (DMSO-d6), δ 7.34 (s, 1H); 6.84 (s, 1H); 2.85-3.10 (m, 1H); 2.43 (s, 3H); 2.32 (s, 3H); 1.70-1.80 (m, 4H); 0.712 (t, J=7.49 Hz, 6H) ppm. MS/ES+=219 (100%, M+2).

Provenance & Evidence