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

HRID 1814928Notes

Reaction equation

HRID 1814928 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 described for CT12440) (12.25 g, 50.0 mmol) and potassium carbonate (6.91 g, 50.0 mmol) in dimethylformamide (400 ml) was added benzyl bromide (9.20 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 (3x 50 ml), ether (3x 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 (3x 50 ml), ether (3x 50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-31a2c1f2092f4d71802eb932bbdb857c
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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