Tetrahydrofuran → 1-(7-Tosyl-7H-pyrrolo[2,3-D]pyrimidin-4-YL)ethan-1-one

HRID 472062Notes

Reaction equation

HRID 472062 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][N:12]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:8]=2[N:9]=[CH:10][N:11]=1)=[CH2:5])C.C1COCC1>CO>[C:21]1([CH3:24])[CH:20]=[CH:19][C:18]([S:15]([N:12]2[C:8]3[N:9]=[CH:10][N:11]=[C:6]([C:4](=[O:3])[CH3:5])[C:7]=3[CH:14]=[CH:13]2)(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 586917324-(1-Ethoxy-vinyl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 586917071-(7-Tosyl-7H-pyrrolo[2,3-D]pyrimidin-4-YL)ethan-1-oneYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[7.25 g, 21.12 mmol] of 4-(1-Ethoxy-vinyl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 50 mL each of methanol and THF and stirred with 10 mL of 6N HCL for 4.0 hours at ambient temperature. The solvents were removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic fraction was brined and dried with anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude material was triturated with a mixture of MTBE and petroleum ether (1:4) for several hours and the solid finally isolated via suction filtration and air dried. The 5.95 g of pale yellow material, representing a 89% yield was used without further purification. 1H NMR: 500 Mhz CDCL3 δ9.0(s,1H), 8.08(d,2H, J=8.4 Hz), 7.87(d, 1H, J=4.1 Hz), 7.3(m,3H), 2.8(s,3H), 2.4(s,3H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution
  3. dry with materialdried with anhydrous sodium sulphate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude material was triturated with a mixture of MTBE and petroleum ether (1:4) for several hours
  6. customthe solid finally isolated via suction filtration and air
  7. customdried
  8. customwas used without further purification

Sources & evidence

ORD record
ord-023b1c2e1a6f48418761d071b94e0df9
Source dataset
uspto-grants-2014_01
Patent number
US08633205B2

Reaction notes

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