[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][N:7]=1.Cl.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:13][CH2:12][N:11]([CH3:15])[CH3:10])[N:7]=1To a solution of 6-chloro-2H-pyridazin-3-one (500 mg, 3.83 mmol) in 5 mL dimethylformamide was added 2-dimethylaminoethyl chloride hydrochloride (828 mg, 5.75 mmol), potassium carbonate (1.59 g, 11.5 mmol) and sodium iodide (632 mg, 4.21 mmol). The mixture was stirred over night at 65° C. Solvent was evaporated. The crude product was dissolved in water and purified by preparative HPLC using a gradient of acetonitrile/5% acetonitrile—water phase containing 0.1 M ammonium acetate, to give 174 mg of 6-chloro-2-(2-dimethylamino-ethyl)-2H-pyridazin-3-one as light brown crystals after freeze drying (22% yield).
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