Potassium Carbonate → HCID 22007301, compound

HRID 323856

Reaction equation

HRID 323856 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][CH2:26][CH3:27])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:28]([O:30][CH2:31]Cl)[CH3:29]>CN(C)C=O.O.CO>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:31][O:30][CH2:28][CH3:29])[C:19](=[O:24])[N:18]([CH2:25][CH2:26][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 18523Chloromethyl ethyl ether2×HCID 220073027-Benzyl-3-propylxanthine

Product 1

HCID 22007301HCID 22007301, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.71 g (12.0 mmol) of potassium carbonate were added to a hot solution of 2.2 g (7.7 mmol) of 7-benzyl-3-propylxanthine from stage a) in 60 ml of dimethylformamide at 60° C. and the mixture was stirred at 60° C. for 1 hour. 0.93 ml (10.0 mmol) of ethoxymethyl chloride was then added dropwise and the mixture was stirred at 80° C. for 4.5 hours. A further 0.5 ml (5.3 mmol) of ethoxymethyl chloride was then added and the mixture was again stirred for 6 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 added again and the mixture was extracted three times using methyl tert-butyl ether. The combined organic phases were washed twice with water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2).

Workup

  1. stirringthe mixture was stirred at 80° C. for 4.5 hours
  2. stirringthe mixture was again stirred for 6 hours
  3. waitto stand overnight
  4. extractionthe mixture was extracted three times
  5. washThe combined organic phases were washed twice with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2)

Sources & evidence

ORD record
ord-fdfe6072ba324e2b8b4432b84f0efb8c
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Linked notes

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