Hydrochloric Acid → (R)-8-bromo-3,7-dimethyl-1-(5-hydroxyhexyl)xanthine

HRID 1835729Notes

Reaction equation

HRID 1835729 reaction equation
C([O:4][C@H:5]([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[C:16]([Br:22])=[N:15][C:14]=2[N:13]([CH3:23])[C:11]1=[O:12])(=O)C.Cl>CO.CCOCC>[Br:22][C:16]1[N:17]([CH3:21])[C:18]2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:24])[C:11](=[O:12])[N:13]([CH3:23])[C:14]=2[N:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54432354HCID 54432354, compound

Product 1

HCID 54015397(R)-8-bromo-3,7-dimethyl-1-(5-hydroxyhexyl)xanthineYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)-1-(5-acetoxyhexyl)-8-bromo-3,7-dimethylxanthine (5.88 g, 14.7 mmol) in methanol (200 ml) was added a solution of hydrogen chloride in ether (1.0 M, 20 ml). The reaction mixture was stirred at room temperature for 24 hours. Evaporation of the solvent under reduced pressure provided (R)-8-bromo-3,7-dimethyl-1-(5-hydroxyhexyl)xanthine (4.8 g, 91% yield) as a white solid.

Workup

  1. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f475e9c1434e455ebe764413ae1a8d3d
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

Loading…