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

HRID 1296403

Reaction equation

HRID 1296403 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-1beba32f5e7e40179fa424f66150ad4c
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Linked notes

Loading…