Benzyl Bromide → 7-Benzyl-3,8-dimethylxanthine

HRID 1835703Notes

Reaction equation

HRID 1835703 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[C:10]([CH3:13])[NH:9][C:8]=2[C:7](=[O:14])[NH:6][C:5]1=[O:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O.CO>[CH2:16]([N:9]1[C:8]2[C:7](=[O:14])[NH:6][C:5](=[O:15])[N:4]([CH3:3])[C:12]=2[N:11]=[C:10]1[CH3:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 179959183,8-Dimethyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 147126087-Benzyl-3,8-dimethylxanthine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of sodium hydroxide (400 mg) in water (5 ml) was added to a suspension of 3,8-dimethylxanthine (1.80 g) in methanol (10 ml). After stirring for 1 hour at 70° C., benzyl bromide (1.2 ml) was added. After stirring for 5 hours at 70-80° C., the solvent was evaporated under reduced pressure. The residue was treated with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (30 ml), dried over magnesium sulfate and concentrated under reduced pressure. The solid was purified by recrystallization from ethanol to provide 7-benzyl-3,8-dimethylxanthine (1.06 g).

Workup

  1. stirringAfter stirring for 5 hours at 70-80° C.
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was treated with saturated aqueous ammonium chloride solution (50 ml)
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (30 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe solid was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-df167e1cbe5f4988b8f7c8480d437196
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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