Sodium Thiosulfate → HCID 71258389, compound

HRID 1506113Notes

Reaction equation

HRID 1506113 reaction equation
[CH:1]1([CH:7]([C:9]2[C:10]3[CH:17]=[CH:16][N:15]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[C:11]=3[N:12]=[CH:13][N:14]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH:1]1([C:7]([C:9]2[C:10]3[CH:17]=[CH:16][N:15]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])[C:11]=3[N:12]=[CH:13][N:14]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71258211HCID 71258211, compound

Product 1

HCID 71258389HCID 71258389, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclohexyl[7-(triisopropylsilyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]methanol (211 mg, 0.540 mmol) in dichloromethane (7 mL) was stirred with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (347 mg, 0.820 mmol) at room temperature for 2.5 hours. After addition of a mixture (1/1 (v/v)) of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulfate, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 (v/v)) to give the title compound as a colorless solid (117 mg, yield 55%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 (v/v))

Sources & evidence

ORD record
ord-424b9bfa92624d3e9cb6ece85d355daa
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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