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

HRID 361504Notes

Reaction equation

HRID 361504 reaction equation
[H-].[Na+].[NH:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5].[CH:16]([CH2:27]S([O-])(=O)=O)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C.O>CS(C)=O>[CH2:25]([N:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 131720764HCID 131720764, compound

Product 1

HCID 158854941-(10-Undecenyl)-3,7-dimethylxanthineYield 46.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 1-(10,11-Oxidoundecanyl)-3,7-dimethylxanthine (inventive compound no. 1594). Sodium hydride(95%) (1.26 g, 50 mmol) was added to a solution of theobromine (7.2 g, 40 mmol) in dimethylsulfoxide (300 mL). After 20 minutes of stirring, undecenylmesylate (7.95 g, 30 mmol) was added and stirred for 12 hours at room temperature. The reaction was warmed to 70°-80° C. and stirred for 4 hours. The reaction mixture was then poured into a separatory funnel containing 1 L of water and extracted with dichloromethane (5×200 mL). The organic extracts are 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 (eluant: 20% hexane/dichloromethane) to yield 4.6 g (46.3% yield) 1-(10-Undecenyl)-3,7-dimethylxanthine (inventive compound no. 2501).

Workup

  1. stirringstirred for 12 hours at room temperature
  2. temperatureThe reaction was warmed to 70°-80° C.
  3. stirringstirred for 4 hours
  4. additionThe reaction mixture was then poured into a separatory funnel
  5. extractionextracted with dichloromethane (5×200 mL)
  6. washwashed with water (100 mL) and brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product obtained
  10. customwas further purified by flash chromatography over silica gel (eluant: 20% hexane/dichloromethane)

Sources & evidence

ORD record
ord-83cde0337f4c436fa9fda38f3b1fb2ff
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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