Bromine → (R)-1-(5-acetoxyhexyl)-8-bromo-3-methylxanthine

HRID 1296413Notes

Reaction equation

HRID 1296413 reaction equation
[C:1]([O:4][C@H:5]([CH3:22])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][CH:16]=[N:15][C:14]=2[N:13]([CH3:21])[C:11]1=[O:12])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:28]Br>C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:22])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([Br:28])=[N:15][C:14]=2[N:13]([CH3:21])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 69155058(R)-1-(5-acetoxyhexyl)-3-methylxanthine

Product 1

HCID 69154488(R)-1-(5-acetoxyhexyl)-8-bromo-3-methylxanthineYield 75.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of (R)-1-(5-acetoxyhexyl)-3-methylxanthine (9.3 g, 30.2 mmol) and sodium acetate (4.92 g, 60.0 mmol) in acetic acid (200 ml) at 60° C. was added bromine (5.76 g, 36.0 mmol) dropwise. After stirring at 60° C. for an additional 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with water (100 ml) and stirred at room temperature for 1 hour. After filtration, the solids were washed with water (3×15 ml) and dried under vacuum to provide (R)-1-(5-acetoxyhexyl)-8-bromo-3-methylxanthine (8.8 g, 75% yield) as a beige powder.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with water (100 ml)
  3. stirringstirred at room temperature for 1 hour
  4. filtrationAfter filtration
  5. washthe solids were washed with water (3×15 ml)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3d931ef03ea841cf8c49d7896021e02c
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

Loading…