Sodium Thiosulfate → 4-(2-Butynyloxy)-6-methanesulfonylpyrimidine

HRID 1759966

Reaction equation

HRID 1759966 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](SC)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].Cl[C:15]1C=CC=C(C(OO)=O)C=1.[S:25]([O-:29])([O-])(=[O:27])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([S:25]([CH3:15])(=[O:29])=[O:27])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 225998774-(2-Butynyloxy)-6-methylthiopyrimidine

Product 1

HCID 225998634-(2-Butynyloxy)-6-methanesulfonylpyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To 14 ml of chloroform were added 4-(2-butynyloxy)-6-methylthiopyrimidine and 3.5 g of m-chloroperbenzoic acid (>65%), followed by stirring at 0° C. for 10 hours. The reaction mixture was then poured into a saturated aqueous sodium thiosulfate solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.4 g of 4-(2-butynyloxy)-6-methanesulfonylpyrimidine.

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4fedc6ac9b4648da863d57e9b653d54c
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Linked notes

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