[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([N:4]1[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([Cl:1])=[N:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=13-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in DMF (300 mL), NaH (3.26 g, 55 wt %) and tetrabutylammoniumiodide (4.60 g) were added at 0° C., and the mixture was stirred at the same temperature for 10 min. To the reaction mixture was added benzylbromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, extracted with dichloromethane, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized from ethyl acetate/hexane to give the title compound (19.8 g).
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