Water → HCID 58485757, compound

HRID 1396143Notes

Reaction equation

HRID 1396143 reaction equation
[I:1][C:2]1[C:10]2[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[C:18]1([S:24]([N:4]2[C:5]3[N:6]=[CH:7][N:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:10]=3[C:2]([I:1])=[CH:3]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 58485736HCID 58485736, compound

Product 1

HCID 58485757HCID 58485757, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-iodo-4-(2-methoxy-ethoxy)-7H-pyrrolo[2,3-d]pyrimidine (25, 3.67 g, 11.5 mmol) in 60.0 mL of tetrahydrofuran under an atmosphere of nitrogen, sodium hydride (506.0 mg, 12.65 mmol) is added. The reaction is stirred at room temperature for 20 minutes, then benzenesulfonyl chloride (26, 1.614 mL, 12.65 mmol) is added. The reaction is stirred at room temperature for 30 minutes, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 15-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (27, 4.50 g). MS (ESI) [M+H+]+=460.0.

Workup

  1. stirringThe reaction is stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with 15-100% ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-59a5610a85a74c4587311646f7e84ac3
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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