Bromine → 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1835709Notes

Reaction equation

HRID 1835709 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].C([O-])(=O)C.[Na+].[Br:18]Br>C(O)(=O)C>[Br:18][C:8]1[NH:7][C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 706393-MethylxanthineHCID 517045Sodium Acetate

Product 1

HCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a stirring suspension of 3-methylxanthine (7.9 g 47.6 mmol) and sodium acetate (7.81 g, 95.2 mmol) in glacial acetic acid (120 ml) was added bromine (9.14 g, 57.1 mmol). The mixture was stirred at 65° C. for 2 hours. After cooling to room temperature the precipitate was filtered, washed with acetic acid (2×15 ml), water (3×50 ml) and dried under vacuum to give 8-bromo-3-methylxanthine (10.5 g, 90% yield) as a beige powder.

Workup

  1. temperatureAfter cooling to room temperature the precipitate
  2. filtrationwas filtered
  3. washwashed with acetic acid (2×15 ml), water (3×50 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f3c6feae6aaf4a7387e1fc26480a3bc4
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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