Sodium hydride → (R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine

HRID 1814923Notes

Reaction equation

HRID 1814923 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]2[N:14]=[CH:13][N:12]([CH3:16])[C:11]=2[C:10](=[O:17])[NH:9][C:8]1=[O:18].[H-].[Na+].[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29]I)(=[O:23])[CH3:22]>CS(C)=O>[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29][N:9]1[C:10](=[O:17])[C:11]2[N:12]([CH3:16])[CH:13]=[N:14][C:15]=2[N:7]([CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:8]1=[O:18])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 224991273-(2-Furylmethyl)-7-methylxanthineHCID 54009360(R)-5-acetoxy-1-iodohexane

Product 1

HCID 54209961(R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthineYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring suspension 3-(2-furylmethyl)-7-methylxanthine (0.40 g, 1.62 mmol) in dimethylsulfoxide (20 ml) was added sodium hydride (41 mg, 1.71 mmol) in one portion. After stirring for 25 minutes, (R)-5-acetoxy-1-iodohexane (0.46 g, 1.71 mol) was added neat. After stirring at room temperature for 72 hours, the reaction was quenched by the addition of water (75 ml) and extracted with ethyl acetate (3x 35 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (2x 35 ml), dried over sodium 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-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine (0.49 g, 78% yield) as a colorless oil.

Workup

  1. stirringAfter stirring at room temperature for 72 hours
  2. customthe reaction was quenched by the addition of water (75 ml)
  3. extractionextracted with ethyl acetate (3x 35 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (2x 35 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-d401e2ed8ca943369323a1e65730887c
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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