Water → 7-Benzyl-8-bromo-3-methylxanthine

HRID 1355395Notes

Reaction equation

HRID 1355395 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:20]([N:10]1[C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=[C:2]1[Br:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 8361527-Benzyl-8-bromo-3-methylxanthineYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 8-bromo-3-methylxanthine (prepared as for CT13430) (12.25 g, 50.0 mmol) and potassium carbonate (6.91 g, 50.0 mmol) in dimethylformamide (400 ml) was added benzyl bromide (9.24 g, 54.0 mmol). After stirring for 12 hours, the mixture was poured into cold water (680 ml). The precipitate was filtered, washed with water (3×50 ml), ether (3×50 ml) and dried under vacuum to provide 7-benzyl-8-bromo-3-methylxanthine (14.92 g, 89% yield) as a white powder.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water (3×50 ml), ether (3×50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-75734d90122e4032a6f6f1d946cc3cf4
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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