CS([O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[N:10]=[C:9]([Cl:18])[N:8]=1)(=O)=O.[F:19][CH2:20][CH:21](O)[CH2:22][F:23].[OH-].[Na+]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:18][C:9]1[N:8]=[C:7]([CH2:6][O:5][CH:21]([CH2:22][F:23])[CH2:20][F:19])[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[N:10]=1To a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (0.50 g, 1.71 mmol) in benzene (10 mL), was added 1,3-difluoro-2-propanol (0.246 g, 2.56 mmol). Sodium hydroxide (5M (aq), 0.512 mL, 2.56 mmol) and tetrabutylammonium hydrogen sulfate (0.058 g, 0.17 mmol) were added. The mixture was stirred vigorously at rt over night. The mixture was filtered through a short silica plug with magnesium sulfate. The filter plug was eluted with EtOAc and the solvents were evaporated. The residue was purified by preparative HPLC to give the title compound as a solid (0.054 g, 11%).
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