[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10](C(Cl)(Cl)Cl)[N:9]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=3)[C:8]=2[CH:23]=1.[O:24]1[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]1>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([O:30][CH:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)[N:9]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=3)[C:8]=2[CH:23]=1Sodium hydride (200 mg, 5.00 mmol, 60% dispersion in mineral oil) was added in several portions into a solution of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol) and oxan-4-ol (1.00 g, 9.79 mmol) in N,N-dimethylformamide (10 mL) under an atmosphere of nitrogen. The reaction mixture was stirred overnight at room temperature and then filtered through a frit filter. The filtrate was purified on a C18 column (acetonitrile/water, 5:95-80:20) to give 170 mg (28%) of 4-[6-bromo-2-(oxan-4-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a brown solid. LC-MS: m/z=+390 (M+H)+.
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