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

HRID 2393355Notes

Reaction equation

HRID 2393355 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 is a method of synthesis for inventive compound no. 3537. 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 the resulting mixture 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 water (1 L) and extracted with five 200 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (100 ml) and brine (100 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, resulting in a crude product, which was further purified by flash chromatography over silica gel using a 20% hexane/dichloromethane eluant producing 4.6 g of 1-(10-undecenyi)-3,7-dimethylxanthine (46.3% yield).

Workup

  1. customa method of synthesis for inventive compound no
  2. stirringthe resulting mixture stirred for 12 hours at room temperature
  3. temperatureThe reaction was warmed to 70°-80° C.` and
  4. stirringstirred for 4 hours
  5. additionThe reaction mixture was then poured into a separatory funnel
  6. extractionextracted with five 200 ml aliquots of dichloromethane
  7. washwashed with water (100 ml) and brine (100 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customresulting in a crude product, which
  11. customwas further purified by flash chromatography over silica gel using a 20% hexane/dichloromethane eluant

Sources & evidence

ORD record
ord-d1730310fa7844a99e73443869033ce1
Source dataset
uspto-grants-1998_09
Patent number
US05807862

Reaction notes

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