Sodium Thiosulfate → 6-Methoxy-4-(methoxycarbonyl)methoxy-2-methylsulfonylpyrimidine

HRID 1862312Notes

Reaction equation

HRID 1862312 reaction equation
Cl[C:2]1C=C(C=CC=1)C(OO)=O.[CH3:12][O:13][C:14]1[N:19]=[C:18](SC)[N:17]=[C:16]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:15]=1.[S:28]([O-:32])([O-])(=[O:30])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14]1[N:19]=[C:18]([S:28]([CH3:2])(=[O:32])=[O:30])[N:17]=[C:16]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:15]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 186191496-Methoxy-4-(methoxycarbonyl)methoxy-2-methylthiopyrimidine

Product 1

HCID 186191946-Methoxy-4-(methoxycarbonyl)methoxy-2-methylsulfonylpyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.59 g of 3-chloroperoxybenzoic acid was added to a solution of 1.22 g of 6-methoxy-4-(methoxycarbonyl)methoxy-2-methylthiopyrimidine in 10 ml of chloroform at 0° C. The mixture was stirred at room temperature for 3 hours, then 30 ml of saturated aqueous sodium thiosulfate solution was added to the mixture. The mixture was poured into saturated aqueous sodium bicarbonate solution, extracted with chloroform, the organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated, then, the resulted residue was subjected to silica gel chromatography to obtain 1.32 g of 6-methoxy-4-(methoxycarbonyl)methoxy-2-methylsulfonylpyrimidine.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-56687f8b62bf45dd94a4930e2edc09c4
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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