Water → HCID 53951389, compound

HRID 1814956Notes

Reaction equation

HRID 1814956 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[C@@H:10]([CH3:28])[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17])(=O)=O.O>CS(C)=O>[N:1]([C@H:10]([CH3:28])[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 54003857HCID 54003857, compound

Product 1

HCID 53951389HCID 53951389, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium azide (7.11 g, 0.1 mol) was added to a solution of (S)-1-(5-methanesulfonyloxyhexyl)-3,7-dimethylxanthine (19.6 g, 54 mmol) in dimethylsulfoxide (100 ml) and stirred at 50° C. for 12 hours. The mixture was treated with water (200 ml) and extracted with ethyl acetate (3x 100 ml). The combined extracts were washed with water (125 ml), with saturated aqueous sodium chloride solution (150 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to give (R)-1-(5-azidohexyl)-3,7-dimethylxanthine (13 g).

Workup

  1. extractionextracted with ethyl acetate (3x 100 ml)
  2. washThe combined extracts were washed with water (125 ml), with saturated aqueous sodium chloride solution (150 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-2f36a353036948a180483b9f196485d6
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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