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

HRID 1870844

Reaction equation

HRID 1870844 reaction equation
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].Br[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH3:20].[H-].[Na+].O>CS(C)=O>[CH2:20]([N:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3])[CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

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 98.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Theobromine (11.9 g, 66 mmol, available from Sigma) was added to a mixture of bromohexene (10.7 g, 66 mmol, available from Aldrich) and sodium hydride (1.58 g, 66 mmol) in dimethylsulfoxide (100 ml) and the resulting mixture stirred for 43 hours. The solution was treated with water (200 ml) and then extracted with three 80 ml aliquots of dichloromethane. The combined extracts were washed with three 100 ml aliquots of water and dried over magnesium sulfate. The solvent was evaporated under vacuum, leaving 17 g of a white powder, 1-(5-hexenyl)-3,7-dimethylxanthine (65 mmol, 98% yield).

Workup

  1. extractionextracted with three 80 ml aliquots of dichloromethane
  2. washThe combined extracts were washed with three 100 ml aliquots of water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-72e406083e07421382fc1fcb63a8f11b
Source dataset
uspto-grants-2000_08
Patent number
US06100271

Linked notes

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