Water → HCID 22007309, compound

HRID 323869Notes

Reaction equation

HRID 323869 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]([CH3:25])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:26]([O:30][CH2:31]Cl)[CH:27]([CH3:29])[CH3:28].O>CN1CCCC1=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:31][O:30][CH2:26][CH:27]([CH3:29])[CH3:28])[C:19](=[O:24])[N:18]([CH3:25])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118609Propane, 1-(chloromethoxy)-2-methyl-2×HCID 6856307-Benzyl-3-methylxanthine

Product 1

HCID 22007309HCID 22007309, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.9 g (14.08 mmol) of potassium carbonate were added at 60° C. to a suspension of 2.25 g (8.8 mmol) of 7-benzyl-3-methylxanthine (prepared according to Example 1 a) in 50 ml of N-methylpyrrolidone and the mixture was stirred at this temperature for one hour. 1.4 g (11.44 mmol) of isobutoxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 3 hours. A further 0.5 g (4.4 mmol) of isobutoxymethyl chloride was then added and the mixture was stirred again for 2 hours. 50 ml of water were then added and the mixture was extracted three times using 60 ml of methyl tert-butyl ether each time. The combined organic phases were washed twice with 30 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, dichloromethane/methanol (19/0.2).

Workup

  1. customprepared
  2. stirringthe mixture was stirred at 80° C. for 3 hours
  3. stirringthe mixture was stirred again for 2 hours
  4. extractionthe mixture was extracted three times
  5. washThe combined organic phases were washed twice with 30 ml of water each time
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19/0.2)

Sources & evidence

ORD record
ord-226ef22ecec244d19ff72d3db1dab115
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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