Barium bromate → 4-(3-Hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

HRID 733190

반응식

HRID 733190 반응식
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]=1

참가 물질

6

반응물 3

HCID 61706Barium bromateHCID 159674Cerous sulfateHCID 690470054-(3-Benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

생성물 1

HCID 578391264-(3-Hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile수율 27.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To 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).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationthen filtered through a sinter glass funnel
  4. washthe residue washed with DCM (10 mL)
  5. washThe filtrate was washed with saturated sodium thiosulphate (10 mL) organics separated
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customsolvent was removed under reduced pressure
  9. customto yield crude product
  10. customPurification by preparative-H PLC

출처 및 근거

ORD 기록
ord-5b4686ede87146bf8431d57f4bb1ca83
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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