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

HRID 367273Notes

Reaction equation

HRID 367273 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

Conditions

Temperature
75 °C

Procedure

This example illustrates a synthesis for compound no. 1592. 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 1 L of water and extracted with dichloromethane (5×200 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 20% hexane and dichloromethane eluent, producing 4.6 g of 1-(10-undecenyl)-3,7-dimethylxanthine (46.3% yield).

Workup

  1. customa synthesis for compound no
  2. stirringthe resulting mixture stirred for 12 hours at room temperature
  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 using 20% hexane and dichloromethane eluent

Sources & evidence

ORD record
ord-d57bc44a4b554bd4a9295489df752025
Source dataset
uspto-grants-2000_10
Patent number
US06133274

Reaction notes

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