Theobromine → 1-(7-Octenyl)-3,7-dimethylxanthine

HRID 1379014

Reaction equation

HRID 1379014 reaction equation
O[CH:2]([CH2:22]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11].[H-].[Na+].N1C(=O)C2N(C)C=NC=2N(C)C1=O.BrCCCCCCC=C>CS(C)=O.O>[CH2:8]([N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:22]

Participants

7

Reactant 4

HCID 5429TheobromineHCID 24758Sodium hydrideHCID 759078-Bromooct-1-eneHCID 97973341-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine

Product 1

HCID 152306341-(7-Octenyl)-3,7-dimethylxanthineYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine (CT1538) was used as an intermediate for the synthesis of CT1514 (example 15). To a suspension of sodium hydride (580 mg, 24.2 mmol) in dimethylsulfoxide (100 ml) was added theobromine (3.96 g, 22.0 mmol). After stirring for 30 min, 8-bromo-1-octene (3.96 g, 22 mmol) was added and the mixture was stirred for 16 hr. The mixture was poured into water (200 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and the solvent was evaporated under vacuum to give 1-(7-octenyl)-3,7-dimethylxanthine (CT1535) (6.22 g, 97% yield) as an oil which solidified upon standing.

Workup

  1. stirringthe mixture was stirred for 16 hr
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-2ce3bf41138e4b8a90a20bc9fcac6066
Source dataset
uspto-grants-1997_09
Patent number
US05670506

Linked notes

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