Sodium Thiosulfate → HCID 86697949, compound

HRID 518787Notes

Reaction equation

HRID 518787 reaction equation
Cl[C:2]1C=C(C=CC=1)C(OO)=O.CS[C:14]1[N:15]=[CH:16][C:17]2[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:18]=2[N:19]=1.[S:33]([O-:37])([O-])(=[O:35])=S.[Na+].[Na+]>ClCCl>[CH3:2][S:33]([C:14]1[N:15]=[CH:16][C:17]2[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:18]=2[N:19]=1)(=[O:37])=[O:35]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86697951Thieno[3,2-d]pyrimidine-6-carboxylic acid, 2-(methylthio)-7-phenyl-, methyl ester

Product 1

HCID 86697949HCID 86697949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.3 g of 3-chloroperoxybenzoic acid (75%) are added slowly, in fractions, to a solution of 1.6 g of methyl 2-(methylsulfanyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate (example 4) in 25 ml of dichloromethane, cooled in an ice bath. The mixture is stirred for 2.5 h while cold, and then left at ambient temperature overnight. The mixture is then diluted with 80 ml of dichloromethane and treated with 60 ml of saturated sodium thiosulfate solution. After stirring and settling out, the aqueous phase is extracted with 60 ml of dichloromethane. The organic phases are washed with 60 ml of a saturated sodium bicarbonate solution, and then with 60 ml of a saturated sodium chloride solution. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to obtain the crude product, which is purified on 200 g of silica, elution being carried out with dichloromethane, so as to obtain 1.4 g of methyl 2-(methylsulfonyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. waitthen left at ambient temperature overnight
  3. stirringAfter stirring
  4. extractionthe aqueous phase is extracted with 60 ml of dichloromethane
  5. washThe organic phases are washed with 60 ml of a saturated sodium bicarbonate solution
  6. dry with materialThe organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum so as
  9. customto obtain the crude product, which
  10. customis purified on 200 g of silica, elution

Sources & evidence

ORD record
ord-5591afcf077f4108b155ecc4948e397a
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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