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

HRID 733190

反应方程式

HRID 733190 反应方程式
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

参与物

6

反应物 3

HCID 61706溴酸钡HCID 159674硫酸亚铈(III)HCID 690470054-(3-Benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

产物 1

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

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6342乙腈溶剂

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-5b4686ede87146bf8431d57f4bb1ca83
来源数据集
uspto-grants-2009_09
专利号
US07589095B2

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