Water → HCID 53812209, compound

HRID 361490Notes

Reaction equation

HRID 361490 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+].CS(O[CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH3:26])(=O)=O.O>CS(C)=O>[CH2:26]([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])[CH2:25][CH2:24][CH:23]=[CH:22][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 54547883HCID 54547883, compound

Product 1

HCID 53812209HCID 53812209, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of theobromine (2.16 g, 12 mmol) and sodium hydride (288 mg, 12 mequivalents) in dimethylsufoxide (10 mL) was stirred for 30 minutes and then a solution of 1-methansulfonyloxy-4-hexene in dimethylsulfoxide (10 mL) was added. After 84 hours of stirring, water (70 mL) is added and the mixture extracted with ether (3×50 mL). The combined extracts were washed with water (50 mL) and dried over magnesium sulfate. The solvent was then evaporated under vacuum. The residue was purified by flash chromatography (22 g silica gel using an ethyl acetate eluant, 500 mL), yielding 2.1 g (67%) 1-(4-hexenyl)-3,7-dimethylxanthine. To a solution of 1-(4-hexenyl)-3,7-dimethylxanthine (270 mg, 1.03 mmol) in dichloromethane (10 mL) was added saturated aqueous sodium bicarbonate solution (10 mL), followed by a solution of 50-60% 3-chloroperoxybenzoic acid (889 mg, 2.58 mmol) in dichloromethane (5 mL) over 1 minute. After 20 hours of stirring, 20% aqueous sodium metabisulfite solution (15 mL) was added over 1 minute. The mixture was then extracted with dichloromethane (3×15 mL). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (3×20 mL) and dried over magnesium sulfate. The sovent was evaporated under vacuum. The residue was purified by flash chromatography using 14 g of silica gel and eluting with ethyl acetate (100 ml) followed by 8% methanol-dichloromethane (60 mL), yielding 80 mg (28% yield) of 1-(4,5-oxohexyl)-3,7-dimethylxanthine as a white powder.

Workup

  1. stirringAfter 84 hours of stirring
  2. extractionthe mixture extracted with ether (3×50 mL)
  3. washThe combined extracts were washed with water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was then evaporated under vacuum
  6. customThe residue was purified by flash chromatography (22 g silica gel using an ethyl acetate eluant, 500 mL),

Sources & evidence

ORD record
ord-f90bb52d5a244d5c9607cd370f5bfb55
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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