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Sodium hydride → (R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

HRID 1421232
Notes
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Reaction equation

HRID 1421232 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]=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31]Cl)(=[O:25])[CH3:24]>CS(C)=O>[C:23]([O:26][C@H:27]([CH3:33])[CH2:28][CH2:29][CH2:30][CH2:31][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)[C:9]([CH3:20])=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110194345-(R)-Acetoxy-1-chlorohexaneHCID 147126087-Benzyl-3,8-dimethylxanthine

Product 1

HCID 54438002(R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

7-Benzyl-3,8-dimethylxanthine (500 mg, 1.85 mmol) was added to a suspension of sodium hydride (50.5 mg) in anhydrous DMSO (20 ml) and stirred for 30 min. (R)-5-acetoxy-1-chlorohexane (357 mg) (prepared according to Kline et al. U.S. Pat. No. 5,629,423 (1997)) was added and the mixture was heated at 70-80° C. for 12 h. After cooling to room temperature, the reaction was quenched by the addition of water (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (silica gel) eluting with ethyl acetate. Yield=638 mg.

Workup

  1. customprepared
  2. addition5,629,423 (1997)) was added
  3. temperatureAfter cooling to room temperature
  4. customthe reaction was quenched by the addition of water (50 ml)
  5. extractionextracted with ethyl acetate (3×75 ml)
  6. washThe combined extracts were washed with water (2×50 ml), with saturated aqueous sodium chloride solution (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (silica gel)
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4f19d0c86fdb439cb02e2a63be4433b0
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06075029

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes