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

HRID 367272Notes

Reaction equation

HRID 367272 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 compound no. 1551 (in addition to the method described in Example 1). 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (compound no. 1561, 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 minutes. 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 minutes. 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 minutes, 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. Recrystalization of the remaining solid was recrystalized in dichloromethane/petroleum ether, resulting in 380 mg of 1-(8,9-oxidononyl)-3,7-dimethylxanthine (91% yield).

Workup

  1. customfor synthesizing compound no
  2. addition1551 (in 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-db797a1799c74e5cbd9256df3d2c80b1
Source dataset
uspto-grants-2000_10
Patent number
US06133274

Reaction notes

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