[CH2:1]([O:3][C:4]1[CH2:5][C:6](=[O:10])[N:7]([CH3:9])[N:8]=1)[CH3:2].Cl[C:12]1[N:13]=[N:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([O:10][C:6]2[N:7]([CH3:9])[N:8]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[N:13]=[N:14][CH:15]=15-Ethoxy-2,4-dihydro-2-methyl-3H-pyrazol-3-one (0.63 g, 0.0044 mole), 3-chloro-5-methoxypyridazine (0.64 g, 0.0044 mole), potassium carbonate (1.50 g, 0.010 mole), cuprous bromide (0.05 g, 0.0003 mole) and anhydrous dimethyl sulfoxide (10 mL) were heated and held at 90° C. for 42 hours. The mixture was cooled, treated with 1% hydrochloric acid solution and extracted with ethyl acetate. The combined extracts were washed with 2% sodium hydroxide, dried with magnesium sulfate, filtered and concentrated in vacuo. Purification by chromatography on silica gel using ethyl acetate/cyclohexane gave a tan solid, which was recrystallized from ethyl acetate/methylcyclohexane to give 5-methoxy-3-[(3-ethoxy-1-methyl-1H-pyrazol-5-yl)oxy]pyridazine (0.22 g, 22% yield) as a white solid.
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