Sodium hydride → (R)-1-(5-Acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthine

HRID 1296404

Reaction equation

HRID 1296404 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[Br: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]([Br:20])=[N:10][C:11]=2[N:12]([CH3:19])[C:13]1=[O:18])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8361527-Benzyl-8-bromo-3-methylxanthineHCID 110194345-(R)-Acetoxy-1-chlorohexane

Product 1

HCID 54190334(R)-1-(5-Acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthineYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring suspension of 7-benzyl-8-bromo-3-methylxanthine (10.06 g, 30.0 mmol) in anhydrous dimethylsulfoxide was added sodium hydride (864 mg, 36.0 mmol). After stirring at room temperature for 30 min, (R)-5-acetoxy-1-chlorohexane (5.9 g, 33.0 mmol) was added. After stirring at 70-75° C. for 12 hours, the mixture was cooled to room temperature, quenched with water (600 ml) and stirred at room temperature for 4 hours. The precipitate was filtered to provide (R)-1-(5-acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthine (12.31 g, 86% yield) as a beige powder.

Workup

  1. stirringAfter stirring at 70-75° C. for 12 hours
  2. temperaturethe mixture was cooled to room temperature
  3. customquenched with water (600 ml)
  4. stirringstirred at room temperature for 4 hours
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-cbc87275f4fc4b3a9bd1e84b4bc4870f
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Linked notes

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