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

HRID 1955973Notes

Reaction equation

HRID 1955973 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-8268615c119649b5b84023e03f3b056c
Source dataset
uspto-grants-1998_07
Patent number
US05777117

Reaction notes

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