Methanol → 4-(6-Chloro-2-methanesulfonyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2053070Notes

Reaction equation

HRID 2053070 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([Cl:20])[N:17]=[C:16](SC)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]O.O[O:26][S:27]([O-:29])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([Cl:20])[N:17]=[C:16]([S:27]([CH3:23])(=[O:29])=[O:26])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 58878061tert-Butyl 4-(6-chloro-2-(methylthio)pyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 588780694-(6-Chloro-2-methanesulfonyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 4-(6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (1 g) in a 10:1 mixture of methanol and water (25 ml) was added oxone® (potassium peroxymonosulfate; 4.1 g). The resulting suspension was stirred at room temperature for 16 hrs. After diluting with water (100 ml), product was extracted into ethyl acetate (100 ml×3) and combined organics were washed with brine (100 ml), dried over MgSO4 and concentrated in vacuo to give 4-(6-chloro-2-methanesulfonyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as a white solid (1.01 g).

Workup

  1. extractionwas extracted into ethyl acetate (100 ml×3)
  2. washcombined organics were washed with brine (100 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5c696c9be6f424bb062c2af0bb99767
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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