3,6-Dichloropyridazine (107,500 mg, 3.36 mmol) was slowly added to 2.0 M methanol solution of methylamine (MeOH solution of NH2Me, 5 mL, 10 mmol) and stirred at room temperature for 24 hours. Upon completion of the reaction, water was added to the reaction mixture and the organic phase was extracted with ethyl acetate. The collected organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography afforded 3-chloro-6-methylaminopyridazine (3-(N-monomethylamino)-6-chloropyridazine, 108e, 505 mg, 88% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 2.84 (d, J = 4.4 Hz, 3H), 6.87 (d, J = 9.2 Hz, 1H), 7.06 (br d, J = 4.0 Hz, 1H), 7.33 (d, J = 9.2 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 27.9, 117.9, 128.2, 144.9, 158.6.
