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

HRID 482259Notes

Reaction equation

HRID 482259 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])[C:6]=2[C:5](=[O:18])[NH:4][C:3]1=[O:19].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=[O:29])[CH3:28].O>CS(C)=O>[O:29]=[C:27]([CH3:28])[CH2:26][CH2:25][CH2:24][CH2:23][N:4]1[C:5](=[O:18])[C:6]2[N:7]([C:11](=[O:17])[C:12]([CH3:15])([CH3:16])[CH2:13][CH3:14])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 250616-Bromohexan-2-oneHCID 215842333-Methyl-7-(methylpivaloyl)xanthine

Product 1

HCID 190638701-(5-Oxohexyl)-3-methyl-7-(methylpivaloyl)xanthineYield 49.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Methyl-7-(methylpivaloyl)xanthine (406 mg, 1.5 mmol) was added to a stirring suspension of NaH (36 mg, 1.5 mmol) in DMSO (20 ml) and stirred for 15 min. 6-Bromo-2-hexanone (260 mg, 1.5 mmol) was added and the reaction mixture was stirred for 20 hrs. The reaction mixture was poured into 100 ml of water and extracted with 25% ethanol/dichloromethane (3×40 ml). The combined organic extracts were combined, dried with magnesium sulfate and the solvent was removed under vacuum to give a brown oil. The brown oil was chromatographed (10 g silica gel, ethyl acetate) to give 1-(5-oxohexyl)-3-methyl-7-(methylpivaloyl)xanthine (270 mg, 49% yield)

Workup

  1. stirringthe reaction mixture was stirred for 20 hrs
  2. extractionextracted with 25% ethanol/dichloromethane (3×40 ml)
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent was removed under vacuum
  5. customto give a brown oil
  6. customThe brown oil was chromatographed (10 g silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-dc437cf957844042a41c7698eea53f26
Source dataset
uspto-grants-1998_08
Patent number
US05795897

Reaction notes

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