C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([S:28](=[O:32])(=[O:31])[NH:29][CH3:30])[CH:19]=2)[N:15]=[C:14]([C:33]#[N:34])[N:13]=1)C1C=CC=CC=1.S([O-])([O-])(=O)=O.[Ce+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Ce+3].Br([O-])(=O)=O.[Ba+2].Br([O-])(=O)=O>C(#N)C.O>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[C:20]([S:28](=[O:32])(=[O:31])[NH:29][CH3:30])[CH:19]=2)[N:15]=[C:14]([C:33]#[N:34])[N:13]=1To a solution of 4-(3-benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (14.4 mg) in acetonitrile (700 μL) and water (300 μL) was added cerium sulphate (3 mg) and barium bromate (6 mg). The mixture was heated to reflux overnight then filtered through a sinter glass funnel, the residue washed with DCM (10 mL). The filtrate was washed with saturated sodium thiosulphate (10 mL) organics separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield crude product. Purification by preparative-H PLC afforded 4-(3-hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (3.2 mg).
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