Hydrogen Bromide → HCID 23295953, compound

HRID 361528Notes

Reaction equation

HRID 361528 reaction equation
[OH:1][CH:2]([CH2:18]O)[CH2:3][CH2:4][N:5]1[C:14](=[O:15])[C:13]2[N:12]([CH3:16])[CH:11]=[N:10][C:9]=2[N:8]([CH3:17])[C:6]1=[O:7].[BrH:20].[C:21](=[O:24])(O)[O-].[Na+].Cl[CH2:27]Cl>C(O)(=O)C>[C:21]([O:1][CH:2]([CH2:18][Br:20])[CH2:3][CH2:4][N:5]1[C:14](=[O:15])[C:13]2[N:12]([CH3:16])[CH:11]=[N:10][C:9]=2[N:8]([CH3:17])[C:6]1=[O:7])(=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23435618HCID 23435618, compound

Product 1

HCID 23295953HCID 23295953, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3,4-Dihydroxybutyl)-3,7-dimethylxanthine (3.98 g, 14.9 mmol) was stirred with hydrogen bromide (9.2 mL, 12.06 g of a 30% solution in acetic acid, 44.7 mmol) for 90 minutes. The mixture was then added to a flask containing 200 mL aqueous saturated sodium bicarbonate solution and 75 mL dichloromethane. After 10 minutes of vigorous stirring, the layers were separated and the aqueous portion washed with dichloromethane (3×150 mL). The organic portions were combined, dried (magnesium sulfate), and evaporated to give 1-(3-acetoxy-4-bromobutyl)-3,7-dimethylxanthine(5.6 g). Without further purification, the bromoacetate was taken up in methanol (50 mL) and treated with a solution of sodium methoxide (prepared from 0.414 g, 12.2 mmol sodium, and 25 mL methanol). After 30 minutes, most of the solvent was removed under reduced pressure and the residue extracted with 25% ethanol/dichloromethane (3×150 mL). The organic portions were combined, dried (magnesium sulfate) and concentrated under reduced pressure to give an off-white solid which is purified by column chromatography over silica gel using an ethyl acetate eluant to yield 2.2 g (58% yield) 1-(3,4-Oxidobutyl)-3,7-dimethylxanthine.

Workup

  1. additionThe mixture was then added to a flask
  2. customthe layers were separated
  3. washthe aqueous portion washed with dichloromethane (3×150 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-9b01dfca1a9e4702a829707209a9863f
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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