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

HRID 269858Notes

Reaction equation

HRID 269858 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.O[O:14][S:15]([O-:17])=O.[K+].O1CCC[CH2:20]1>O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][S:10][C:4]=2[N:5]=[C:6]([S:15]([CH3:20])(=[O:17])=[O:14])[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

Procedure

To a solution of 4-chloro-2-methylsulfanyl-thieno[2,3-d]pyrimidine (10 g, 46.15 mmol) in tetrahydrofuran (350 mL) at 0° C. was added a solution of OXONE (59.6 g, 2.1 eq) in water (300 mL) dropwise with stirring. The resulting mixture was gradually warmed from 0° C. to room temperature overnight. The reaction mixture was diluted with ethyl acetate (1000 mL) and water (300 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (1×300 mL). Organic layers were combined, washed with brine (2×300 mL), dried over magnesium sulfate, filtered and concentrated to give 10.7 g of the title compound as a tan powder (M+H)+=249.

Workup

  1. temperatureThe resulting mixture was gradually warmed from 0° C. to room temperature overnight
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (1×300 mL)
  4. washwashed with brine (2×300 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-41861c46e6c2404d99d55c98b6723843
Source dataset
uspto-grants-2008_11
Patent number
US07449472B2

Reaction notes

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