Water → HCID 22007320, compound

HRID 323863Notes

Reaction equation

HRID 323863 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[NH:20][C:19](=[O:24])[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:31]([O:34][CH2:35]Cl)[CH2:32][CH3:33].O>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:35][O:34][CH2:31][CH2:32][CH3:33])[C:19](=[O:24])[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 104957677-Benzyl-3-phenylxanthineHCID 109644311-(Chloromethoxy)propane

Product 1

HCID 22007320HCID 22007320, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.45 g (3.26 mmol) of potassium carbonate was added at 60° C. to a suspension of 0.65 g (2.04 mmol) of 7-benzyl-3-phenylxanthine from stage a) in 20 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 0.29 ml (2.65 mmol) of propoxymethyl chloride was then added dropwise and the mixture was stirred at 80° C. for 1.5 hours. 20 ml of water were then added, the mixture was extracted three times using 24 ml of methyl tert-butyl ether each time, and the combined organic phases were washed twice with 12 ml of water each time, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column heptane/ethyl acetate (5/7).

Workup

  1. stirringthe mixture was stirred at 80° C. for 1.5 hours
  2. extractionthe mixture was extracted three times
  3. washthe combined organic phases were washed twice with 12 ml of water each time
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on a silica gel column heptane/ethyl acetate (5/7)

Sources & evidence

ORD record
ord-c814146947084c3e9d675de9cf8f3330
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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