Tetrahydrofuran → 4-Chloro-2-methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 1694849Notes

Reaction equation

HRID 1694849 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:16][C:8]2[N:9]=[C:10](SC)[N:11]=[C:12]([Cl:13])[C:7]=2[CH:6]=1)=[O:4].O[O:18][S:19]([O-:21])=O.[K+].[CH2:23]1COCC1>O>[CH3:1][O:2][C:3]([C:5]1[S:16][C:8]2[N:9]=[C:10]([S:19]([CH3:23])(=[O:21])=[O:18])[N:11]=[C:12]([Cl:13])[C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59376433Methyl 4-chloro-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 593764254-Chloro-2-methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-chloro-2-methylsulfanyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (3.3 g, 12.0 mmol) in THF (150 mL) was added a solution of Oxone (15.5 g, 25.2 mmol) in H2O (80 mL) dropwise at RT. After 18 h, the solvent was removed and the residue was diluted with CH2Cl2. The organic fraction was washed with water (1×), brine (1×), dried over. MgSO4, and concentrated. The residue was used without further purification. ESIMS calcd 307 (M++H), found 307 (M++H).

Workup

  1. customthe solvent was removed
  2. additionthe residue was diluted with CH2Cl2
  3. washThe organic fraction was washed with water (1×), brine (1×)
  4. customdried over
  5. concentrationMgSO4, and concentrated
  6. customThe residue was used without further purification

Sources & evidence

ORD record
ord-460bc04865d84d25a1ae69489b648e27
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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