[H-].[Na+].[CH:3]1([CH:6]([C:8]2[C:13]3[N:14]4[CH2:20][CH2:19][CH2:18][N:17]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])[C:15]4=[N:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)[OH:7])[CH2:5][CH2:4]1.[CH3:29]I>CN(C)C=O.O>[CH:3]1([CH:6]([O:7][CH3:29])[C:8]2[C:13]3[N:14]4[CH2:20][CH2:19][CH2:18][N:17]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])[C:15]4=[N:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4]1Sodium hydride (60% in oil, 45.3 mg, 1.13 mmol) was added to a stirred solution of cyclopropyl[1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (400 mg, 1.03 mmol) in N,N-dimethylformamide (3.0 mL) at 0° C. After stirring 5 min, methyl iodide (219 mg, 1.55 mmol) was added to the mixture, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless crystal (265 mg, 0.659 mmol, 64%).
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