Potassium Carbonate → HCID 22007314, compound

HRID 323861Notes

Reaction equation

HRID 323861 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]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:29]([O:32][CH2:33]Cl)[CH2:30][CH3:31]>CN(C)C=O.O.CO>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:33][O:32][CH2:29][CH2:30][CH3:31])[C:19](=[O:24])[N:18]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 30174687-Benzyl-3-(2-methylpropyl)xanthineHCID 109644311-(Chloromethoxy)propane

Product 1

HCID 22007314HCID 22007314, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.86 g (6.2 mmol) of potassium carbonate was added at 60° C. to a suspension of 1.16 g (3.9 mmol) of 7-benzyl-3-isobutylxanthine from stage c) in 60 ml of dimethylformamide and the mixture was stirred at this temperature for 1 hour. 0.56 ml (5.1 mmol) of propoxymethyl chloride was then added dropwise and the mixture was stirred at 80° C. for 5.5 hours. 12 ml of water and 5 ml of methanol were then added, the mixture was allowed to stand overnight, 60 ml of water were again added and the mixture was extracted four times using 150 ml of methyl tert-butyl ether each time. The combined organic phases were washed with 200 ml of water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane.

Workup

  1. stirringthe mixture was stirred at 80° C. for 5.5 hours
  2. waitto stand overnight
  3. extractionthe mixture was extracted four times
  4. washThe combined organic phases were washed with 200 ml of water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane

Sources & evidence

ORD record
ord-c947d333f5f6417d8fe25a4d472516ae
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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