Benzenesulfonyl chloride → 5-Iodo-7-(phenylsulfonyl)-7H-Pyrrolo[2,3-d]pyrimidine

HRID 1692827Notes

Reaction equation

HRID 1692827 reaction equation
[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:13]1([S:19]([N:4]2[C:5]3[N:6]=[CH:7][N:8]=[CH:9][C:10]=3[C:2]([I:1])=[CH:3]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 106103365-Iodo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579630495-Iodo-7-(phenylsulfonyl)-7H-Pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Iodo-7H-pyrrolo[2,3-d]pyrimidine (39, 0.569 g, 2.32 mmol) was added to 10.0 mL of N,N-dimethylformamide in a round bottom flask. Sodium hydride (0.102 g, 2.55 mmol) was added and the reaction stirred at room temperature for 10 minutes, then benzenesulfonyl chloride (40, 326 μL, 2.55 mmol) was added. The reaction was stirred at room temperature overnight, then poured into aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate adsorbed onto silica. The desired compound was isolated by silica gel column chromatography, eluting with 0.5-6% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum. Toluene was added to the residue, then concentrated under vacuum and the resulting solid was washed with hexane and collected by filtration to provide the desired compound (41, 439 mg). 1H NMR consistent with the compound structure.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-506da16243544247a1a147a6536cdbc6
Source dataset
uspto-grants-2012_04
Patent number
US08158636B2

Reaction notes

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