Sodium Thiosulfate → Methyl 2-(methanesulfonyl)pyrimidine-5-carboxylate

HRID 219671Notes

Reaction equation

HRID 219671 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](SC)=[N:9][CH:10]=1)=[O:4].[CH:13]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:24][S:25]([O-:28])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([S:25]([CH3:13])(=[O:28])=[O:24])=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylate

Product 1

HCID 53396491Methyl 2-(methanesulfonyl)pyrimidine-5-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylsulfanyl-pyrimidine-5-carboxylic acid methyl ester 1 (1 g, 5.43 mmol) in DCM (60 mL) is added MCPBA (2.81 g, 16.29 mmol) portion wise at room temperature. The resulting solution is stirred at room temperature overnight. A solution of Na2S2O3 (1.6 g) in water (60 mL) is added. The mixture is stirred at room temperature for 20 min. The layer is separated, and the water layer is extracted with DCM (2×20 mL). The combined DCM layer is washed with saturated NaHCO3 (3×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 2-methanesulfonyl-pyrimidine-5-carboxylic acid methyl ester as a solid (1.05 g, 90%). MS: 217 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.41 (s, 3H), 4.06 (s, 3H), 9.44 (s, 2H).

Workup

  1. stirringThe mixture is stirred at room temperature for 20 min
  2. customThe layer is separated
  3. extractionthe water layer is extracted with DCM (2×20 mL)
  4. washThe combined DCM layer is washed with saturated NaHCO3 (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bab0c6a785ff4f04be7cf4774c1a7229
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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