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

HRID 2200536Notes

Reaction equation

HRID 2200536 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 966.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-methyl-1H-purine-2,6(3H,7H)-dione (11.3 g, 6.8 mmol) in acetic acid (300 mL) was added sodium acetate (8.37 g, 13.6 mmol) followed by drop-wise addition of bromine (13.04 g, 8.2 mmol) at 50° C. After addition, the mixture was stirred at 65° C. for 3 h. The mixture was cooled and poured into ice-water (500 g), and the product precipitated. The slurry was filtered and the filter cake was washed with water twice and dried under vacuum to give 8-bromo-3-methyl-1H-purine-2,6(3H,7H)— dione (16.1 g, 96.6% yield) as light yellow solid. LCMS retention time 0.541 min; LCMS MH+ 245.

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled
  3. customthe product precipitated
  4. filtrationThe slurry was filtered
  5. washthe filter cake was washed with water twice
  6. customdried under vacuum

Sources & evidence

ORD record
ord-99161fc9186b4264a7081094e87c6f14
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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