Sodium hydride → 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1814929Notes

Reaction equation

HRID 1814929 reaction equation
C([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])C1C=CC=CC=1.[H-].[Na+].C(O[C@H](C)CCCCCl)(=O)C>CS(C)=O>[Br:20][C:9]1[NH:8][C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=1

Participants

5

Reactant 3

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

Product 1

HCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneYield 167.5%

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-benzy)-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-ceba2a662eac47638e9643a1646af8f4
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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