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

HRID 1379008Notes

Reaction equation

HRID 1379008 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[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>[CH2:2]([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])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 759066-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 (CT1541) was synthesized and used as an intermediate for synthesizing CT1517 and CT1595 as described in examples 2 and 3 below. A mixture of 1-bromo-5-hexene (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 hr. 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 (CT1539) (17 g, 98% yield) as a white powder.

Workup

  1. customused as an intermediate for synthesizing CT1517 and CT1595
  2. extractionextracted with dichloromethane (3×80 ml)
  3. washThe combined extracts were washed with water (3×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-a11b694886fe410cb17d46d6c86ddf2c
Source dataset
uspto-grants-1997_09
Patent number
US05670506

Reaction notes

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