Sodium Thiosulfate → 2-Chloro-4-(methanesulfonyl)pyrimidine

HRID 595152Notes

Reaction equation

HRID 595152 reaction equation
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:12][C:13]1[N:18]=[C:17](SC)[CH:16]=[CH:15][N:14]=1.C(=O)(O)[O-].[Na+].[S:26]([O-:30])([O-])(=[O:28])=S.[Na+].[Na+]>ClCCl>[Cl:12][C:13]1[N:18]=[C:17]([S:26]([CH3:1])(=[O:30])=[O:28])[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 164271482-Chloro-4-(methylthio)pyrimidine

Product 1

HCID 197713792-Chloro-4-(methanesulfonyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (3.92 g, 17.5 mmol) was added to a stirred mixture of 2-chloro-4-(methylsulfanyl)pyrimidine (1.5 g, 7.0 mmol) in dichloromethane (35.0 mL) at 0° C. The reaction mixture was warmed to room temperature, stirred for 1.5 h and then diluted with aqueous sodium thiosulfate. The solution was stirred for 10 min then saturated sodium bicarbonate was added and the mixture was extracted with dichloromethane. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford 2-chloro-4-(methylsulfonyl)pyrimidine as a white solid. MS ESI calcd. for C5H6C1N2O2S [M+H]+ 193. found 193.

Workup

  1. stirringThe solution was stirred for 10 min
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6e2e90bdaf0e4e19847728ccaace99be
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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