Water → 1-(6-Hydroxyhexyl)-3,7-dimethylxanthine

HRID 1637654Notes

Reaction equation

HRID 1637654 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].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].O>CS(C)=O>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][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]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 779706-Bromo-1-hexanol

Product 1

HCID 99256901-(6-Hydroxyhexyl)-3,7-dimethylxanthineYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example is a synthesis for inventive compound no. 1527 (see above for chemical name and structure). A mixture of theobromine (1.0 g, 5.5 mmol, available from Sigma) and a solution (20 ml) of 50% sodium hydride in oil (264 mg, 5.5 mmol) in dimethylsulfoxide was stirred for 50 minutes, followed by addition of 6-bromo-1-hexanol (1.0 g, 5.5 mmol, available from Aldrich). After stirring for 18 hours, the solution was treated with 50 ml of water and then extracted with two 25 ml aliquots of hexanes. The aqueous phase was extracted with three 35 ml aliquots of 25% ethanol-dichloromethane. The combined ethanol-dichloromethane extracts were dried over magnesium sulfate and then the solvents were evaporated under vacuum. The remaining dimethylsulfoxide was removed by distillation under full pump vacuum, producing 1.4 g of a white powder, 1-(6-hydroxyhexyl)-3,7-dimethylxanthine (5.0 mmol, 91% yield).

Workup

  1. customa synthesis for inventive compound no
  2. extractionextracted with two 25 ml aliquots of hexanes
  3. extractionThe aqueous phase was extracted with three 35 ml aliquots of 25% ethanol-dichloromethane
  4. dry with materialThe combined ethanol-dichloromethane extracts were dried over magnesium sulfate
  5. customthe solvents were evaporated under vacuum
  6. customThe remaining dimethylsulfoxide was removed by distillation under full pump vacuum

Sources & evidence

ORD record
ord-73b7821b7f374da18db76c32e9428bc3
Source dataset
uspto-grants-2000_03
Patent number
US06043250

Reaction notes

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