[F:1][C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1.Cl[C:22]1[CH:34]=[C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:35])[N:23]=1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)[CH2:19][O:20][C:22]1[CH:34]=[C:26]2[N:27]([CH:31]([CH3:32])[CH3:33])[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:35])[N:23]=1To a solution of (3-fluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol (126 mg, 0.439 mmol) and 8-chloro-1-isopropyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (20 mg, 0.088 mmol) in N,N-dimethylformamide (DMF) (8 mL), was added NaH (35.1 mg, 0.878 mmol) 25 and stirred for 1 h at rt. The reaction mixture was quenched by addition of sat. aq. NH4Cl solution and was filtered. The solution was purified by MDAP to afford the desired product as a white solid.
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