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

HRID 1421231Notes

Reaction equation

HRID 1421231 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

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) at 70° C. and stirred for 1 hour. Benzyl bromide (1.2 ml) was added and the mixture was stirred at 70-80° C. for 5 hours. After evaporation of the solvent under reduced pressure, the residue was suspended in 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 concentrate. The product was purified by recrystallization from ethanol. Yield=1.06 g.

Workup

  1. stirringthe mixture was stirred at 70-80° C. for 5 hours
  2. customAfter evaporation of the solvent under reduced pressure
  3. extractionextracted with ethyl acetate (3×75 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrate
  7. customThe product was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-abed677c7c934476abfd167829b6f730
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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