Water → 1-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 356613Notes

Reaction equation

HRID 356613 reaction equation
Br[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[NH:10]1[C:21](=[O:22])[C:20]2[N:18]([CH3:19])[CH:17]=[N:16][C:15]=2[N:13]([CH3:14])[C:11]1=[O:12].O>CS(C)=O>[CH2:7]([N:10]1[C:21](=[O:22])[C:20]2[N:18]([CH3:19])[CH:17]=[N:16][C:15]=2[N:13]([CH3:14])[C:11]1=[O:12])[CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 2873381-Bromo-1-hexene

Product 1

HCID 128776801-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dioneYield 98.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(5,6-Oxidohexyl)-3,7-dimethylxanthine was synthesized as follows: A mixture of 1-bromohexene (10.7 g, 66 mmol), sodium hydride (1.58 g, 66 mmol), and theobromine (11.9 g, 66 mmol) in dimethylsulfoxide (100 ml) was stirred for 43 hours. The solution was treated with water (200 ml) and then extracted with dichloromethane (3×80 mL). The combined extracts were washed with water (3×100 ml), dried over magnesium sulfate, and then the solvent was evaporated under vacuum to give 1-(5-hexenyl)-3,7-dimethylxanthine (17 g, 98% yield) as a white powder.

Workup

  1. extractionextracted with dichloromethane (3×80 mL)
  2. washThe combined extracts were washed with water (3×100 ml)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-d92bee83b85c41e494f6839418a57b87
Source dataset
uspto-grants-1998_11
Patent number
US05837703

Reaction notes

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