Water → 4-[2-Methanesulfonyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 2053087Notes

Reaction equation

HRID 2053087 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[N:18]=[C:17](SC)[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:33]([O-:38])(O[O-])(=O)=[O:34].[K+].[K+].O.[C:42](#N)C>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)[N:18]=[C:17]([S:33]([CH3:42])(=[O:38])=[O:34])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 10313463Potassium peroxymonosulphateHCID 688232604-[2-Methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 688257784-[2-Methanesulfonyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[2-Methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (185 mg) and potassium peroxymonosulfate (558 mg) were stirred at room temperature in acetonitrile (3 ml) and water (300 μl) for eight hours. Reaction mixture was then diluted with ethyl acetate (50 ml) and washed with water (2×40 ml). Organics were separated, dried over sodium sulphate and solvent was evaporated under reduced pressure to yield product 4-[2-methanesulfonyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (139 mg) as a yellow gum. MS m/z 501.3 (M+1).

Workup

  1. customReaction mixture
  2. washwashed with water (2×40 ml)
  3. customOrganics were separated
  4. dry with materialdried over sodium sulphate and solvent
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-d055dbbc7fbc49b2a1306a651296b0f7
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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