Water → 7-(10-Undecenyl)-1,3-dimethylxanthine

HRID 1954098Notes

Reaction equation

HRID 1954098 reaction equation
[H-].[Na+].[N:3]1([C:14](=[O:15])[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[N:7]([CH3:8])[C:5]1=[O:6])[CH3:4].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].O>CS(C)=O>[CH2:27]([N:12]1[C:13]2[C:14](=[O:15])[N:3]([CH3:4])[C:5](=[O:6])[N:7]([CH3:8])[C:9]=2[N:10]=[CH:11]1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 2153TheophyllineHCID 24758Sodium hydrideHCID 28414811-Bromo-1-undecene

Product 1

HCID 154105187-(10-Undecenyl)-1,3-dimethylxanthineYield 94.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 7-(11,10-Oxidondecyl)-1,3-dimethylxanthine (inventive compound no. 1423). Sodium hydride (95%) (0.575 g, 24 mmol) was added to a solution of theophylline (3.6 g, 20 mmol) in dimethylsulfoxide (100 mL). After 20 minutes of stirring, 1-bromoundec-10-ene (4.66 g, 20 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing water (300 mL) and extracted with dichloromethane (5×100 mL). The organic extracts were combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 50% hexane/ethyl acetate eluant, yielding 6.26 g (94% yield) of 7-(10-undecenyl)-1,3-dimethylxanthine (inventive compound no. 1420).

Workup

  1. stirringstirred for 12 hours at room temperature
  2. additionThe reaction mixture was then poured into a separatory funnel
  3. extractionextracted with dichloromethane (5×100 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel using 50% hexane/ethyl acetate eluant

Sources & evidence

ORD record
ord-cea9f85fd69f459f84a6cc28e65fa8f6
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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