Acetic Acid → 1-(8-Acetoxy-9-bromononyl)-3,7-dimethylxanthine

HRID 1954107Notes

Reaction equation

HRID 1954107 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]([OH:29])(=O)[CH3:27].C(=O)(O)[O-]>ClCCl.O>[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])[CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 769Bicarbonate IonHCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine and 30% hydrogen bromide in acetic acid (0.8 mL, 3.90 mmol) was stirred for 90 minutes. The solution was poured into a mixture of water (10 mL), sodioum bicarbonate (1.35 g, and dichloromethane (10 mL). After 10 minutes of vigorous stiring, the layers were separated and the aqueous portion extracted with dichloromethane (3×15 mL). The combined organic phases were dried over sodium sulfate and the solvent evaporated under vacuum, yielding 550 mg (96%) 1-(8-acetoxy-9-bromononyl)-3,7-dimethylxanthine as a yellow oil. Without further purification, the oil was dissoved in methanol (5 mL) and then a 1 M solution of sodium methoxide in methanol (1.4 mL) was added. After 30 minutes, the reaction mixture was poured into water (30 mL) and was extracted with dichloromethane (3×40 mL). The combined organic portions were dried over sodium sulfate and the solvents evaporated under vacuum. The solid residue was recrystallized (dichloromethane-petroleum ether) to yield 380 mg (91% yield) 1-(8,9-oxidononyl)-3,7-dimethylxanthine (inventive compound no. 1560).

Workup

  1. waitAfter 10 minutes of vigorous stiring
  2. customthe layers were separated
  3. extractionthe aqueous portion extracted with dichloromethane (3×15 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-d367d93e05434895884498f8e3a7122f
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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