Water → 1-(8-Nonenyl)-3,7-dimethylxanthine

HRID 2259421Notes

Reaction equation

HRID 2259421 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([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28])(=O)=O.O>CS(C)=O.C(OCC)(=O)C>[CH2:28]([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])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=[CH2:20]

Participants

7

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 232879369-Methanesulfonyl-1-nonene

Product 1

HCID 152306351-(8-Nonenyl)-3,7-dimethylxanthineYield 26%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Theobromine (1.98 g, 11 mmol) was added to a suspension of NaH (600 mg of a 50% mineral oil slurry, 12 mmol) in DMSO (15 ml). After 15 min, 9-methanesulfonyl-1-nonene (2.25 g, 11 mmol) was added and the reaction mixture was stirred for 6 days at 25° C. The reaction mixture was poured into 60 ml of water and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried with magnesium sulfate, and evaporated to give a dark oil. Chromatography (silica, ethyl acetate) gave 1-(8-nonenyl)-3,7-dimethylxanthine (CT1550) as a colorless oil (810 mg, 26% yield).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. dry with materialdried with magnesium sulfate
  3. customevaporated
  4. customto give a dark oil

Sources & evidence

ORD record
ord-2ddea1adb2ef42ddb192c8a8818c22ab
Source dataset
uspto-grants-1995_12
Patent number
US05473070

Reaction notes

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