[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)C=O.[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]=1
3-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in N,N-dimethylformamide (300 mL), sodium hydride (3.26 g, 55 wt %) and tetrabutylammonium iodide (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 benzyl bromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, and extracted with dichloromethane. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate/hexane gave the title compound (19.8 g).
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