Water → 1-(5-Hexenyl)-3-methyl-7-(methylpivaloyl)xanthine

HRID 1954096Notes

Reaction equation

HRID 1954096 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13](=[O:19])[C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])[C:8]=2[C:7](=[O:20])[NH:6][C:5]1=[O:21].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28].O>CS(C)=O.C(OCC)(=O)C>[CH2:28]([N:6]1[C:7](=[O:20])[C:8]2[N:9]([C:13](=[O:19])[C:14]([CH3:17])([CH3:18])[CH2:15][CH3:16])[CH:10]=[N:11][C:12]=2[N:4]([CH3:3])[C:5]1=[O:21])[CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 215842333-Methyl-7-(methylpivaloyl)xanthine

Product 1

HCID 232959671-(5-Hexenyl)-3-methyl-7-(methylpivaloyl)xanthineYield 69.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (86 mg, 3.6 mmol) was added to a stirring solution of 3-methyl-7-(methylpivaloyl)xanthine 1404 (1.00 g, 3.6 mmol) in dimethyl sulfoxide (25 mL). After 15 minutes, 6-bromo-1-hexene (589 mg, 3.6 mmol) was added and stirring continued for 72 hours. The reaction mixture was then poured into water (70 mL) and extracted with dichloromethane (2×100 mL) and 20% ethanol/dichloromethane (1×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL) and dried over magnesium sulfate. The solvent was evaporated under vacuum to give a thick oil. Chromotograpy of the resulting thick oil using silica and ethyl acetate yielded 870 mg (67% yield) 1-(5-hexenyl)-3-methyl-7-(methylpivaloyl)xanthine (inventive compound no. 1441)

Workup

  1. waitcontinued for 72 hours
  2. extractionextracted with dichloromethane (2×100 mL) and 20% ethanol/dichloromethane (1×100 mL)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under vacuum
  6. customto give a thick oil

Sources & evidence

ORD record
ord-1049e0dca6dd4427aa26898ea72a98fd
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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