Sodium hydride → (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine

HRID 1814946Notes

Reaction equation

HRID 1814946 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30]Br)(=[O:24])[CH3:23]>CS(C)=O>[C:22]([O:25][C@@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][N:14]1[C:15](=[O:17])[C:16]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6856307-Benzyl-3-methylxanthineHCID 54040544(S)-5-acetoxy-1-bromohexane

Product 1

HCID 53701359(S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthineYield 87.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring suspension of 7-benzyl-3-methylxanthine (0.512 g, 2 mmol) in dimethyl sulfoxide (10 ml) was added 95% sodium hydride (50.5 mg, 2.0 mmol) in one portion. After stirring for 30 minutes, (S)-5-acetoxy-1-bromohexane (0.490 g, 2.2 mmol) was added neat. After stirring at room temperature for 12 hours, the reaction was quenched by addition of water (50 ml) and extracted with ethyl acetate (3x 50 ml). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml) and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate to give (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (0.700 g).

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. customthe reaction was quenched by addition of water (50 ml)
  3. extractionextracted with ethyl acetate (3x 50 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 ml), with saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent under reduced pressure
  7. customgave a residue which
  8. customwas purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-90084666789343a39c44521a6a22e546
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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