Tetrahydrofuran → 4-Chloro-2-(methylsulfonyl)thieno[2,3-d]pyrimidine

HRID 19569Notes

Reaction equation

HRID 19569 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][S:10][C:4]=2[N:5]=[C:6](SC)[N:7]=1.[CH2:13]1COCC1.O[O:19][S:20]([O-:22])=O.[K+]>O.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][S:10][C:4]=2[N:5]=[C:6]([S:20]([CH3:13])(=[O:22])=[O:19])[N:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 219883514-Chloro-2-(methylthio)thieno[2,3-d]pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 219883544-Chloro-2-(methylsulfonyl)thieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 1 L round-bottom flask was added 4-chloro-2-(methylthio)thieno[2,3-d]pyrimidine (35.0 g, 162 mmol), THF (300 mL). The solution was stirred at 0° C. and treated dropwise with a solution of OXONE (209 g, 339 mmol) in water (350 mL). The resulting mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc (500 mL) and water (300 mL). Separated the layers, the aqueous layer was extracted with EtOAc (3×300 mL). Organic layers were combined, washed with brine (2×300 mL), dried over MgSO4, filtered and concentrated to give (33 g). MS (ES+): 249 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customSeparated the layers
  3. extractionthe aqueous layer was extracted with EtOAc (3×300 mL)
  4. washwashed with brine (2×300 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give (33 g)

Sources & evidence

ORD record
ord-03422f858edf4ef7aae928893ffd282e
Source dataset
uspto-grants-2010_06
Patent number
US07745449B2

Reaction notes

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