Water → HCID 22861486, compound

HRID 361539Notes

Reaction equation

HRID 361539 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].[Na].CS([CH2:19][CH2:20][CH2:21][C@H:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])(=O)=O.O>CS(C)=O>[CH3:29][C@H:22]([CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH2:21][CH2:20][CH2:19][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

5

Reactant 3

HCID 962WaterHCID 22861489HCID 22861489, compoundHCID 66980828Theobromine sodium

Product 1

HCID 22861486HCID 22861486, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium theobromine (4.05 g, 20.0 mmol) in dimethylsulfoxide (50 mL) was added 1-methanesulfonyl-4-(R)-methyl-8-methylnon-7-ene and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (100 mL) and extracted with ethyl acetate (100 mL, 2×50 mL). The organic portions were combined, dried using magnesium sulfate and the solvent evaporated to give a residue which was purified by column chromatography using ethyl acetate/hexane to yield 1.70 g (28% yield) 1-(4-(R)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine (inventive compound no. 2536R) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (100 mL, 2×50 mL)
  2. customdried
  3. customthe solvent evaporated
  4. customto give a residue which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-45e6229384324b8e84a5d9e8805641aa
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

Loading…