Hydrogen Bromide → 1-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthine

HRID 2259423Notes

Reaction equation

HRID 2259423 reaction equation
[OH:1][CH:2]([CH2:23]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12].[BrH:25].[C:26](=[O:29])(O)[O-].[Na+].Cl[CH2:32]Cl>C(O)(=O)C>[C:26]([O:1][CH:2]([CH2:23][Br:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

Product 1

HCID 153385971-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthineYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This example illustrates another method for synthesizing CT1551 (in addition to the method described in Example 1). CT1561 (1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine) (428 mg, 1.3 mmol) was stirred with HBr (777 μl, 1.05 g of a 30% solution in acetic acid, 3.9 mmol) for 90 min. The mixture was then added to a flask containing aqueous sodium bicarbonate solution (10 ml, 1.35 g) and dichloromethane (10 ml) and stirred vigorously for 10 min. The layers were separated and the aqueous portion was washed with dichloromethane (3×15 ml). The organic portions were combined, dried with sodium sulfate and evaporated to give 1-(8-acetoxy-9-bromononyl)-3,7-dimethylxanthine as a yellow oil (550 mg, 96% yield). Without further purification, the oil was taken up in methanol (5 ml) and treated with a solution of sodium methoxide (prepared from 33 mg, 1.4 mmol sodium and 1.4 ml methanol). After 30 min the reaction mixture was added to water (30 ml) and extracted with dichloromethane (3×40 ml). The organic portions were combined and dried to give an off-white solid which was recrystalized in dichloromethane/petroleum ether to give 1-(8,9-oxidononyl)-3,7-dimethylxanthine (CT1560) (380 mg, 91%).

Workup

  1. customfor synthesizing CT1551 (
  2. additionin addition to the method
  3. additionThe mixture was then added to a flask
  4. customThe layers were separated
  5. washthe aqueous portion was washed with dichloromethane (3×15 ml)
  6. dry with materialdried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-ca1f983b9bcd4f8da7b26fd15178c9f0
Source dataset
uspto-grants-1995_12
Patent number
US05473070

Reaction notes

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