Water → 7-Benzyl-1-butoxymethyl-3-isopropylxanthine

HRID 323868Notes

Reaction equation

HRID 323868 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]([CH:25]([CH3:27])[CH3:26])[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:32][CH2:33]Cl)[CH2:29][CH2:30][CH3:31].O>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:33][O:32][CH2:28][CH2:29][CH2:30][CH3:31])[C:19](=[O:24])[N:18]([CH:25]([CH3:27])[CH3:26])[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 111053571-(Chloromethoxy)butane2×HCID 220072987-Benzyl-3-isopropylxanthine

Product 1

HCID 220072997-Benzyl-1-butoxymethyl-3-isopropylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.583 g (4.22 mmol) of potassium carbonate was added at 60° C. to a suspension of 0.75 g (2.64 mmol) of 7-benzyl-3-isopropylxanthine from stage a) in 20 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 0.42 g (3.43 mmol) of butoxymethyl chloride was then added dropwise and the mixture was stirred at 80° C. for 6 hours. A further 0.11 g (0.87 mmol) of butoxymethyl chloride was then added and the mixture was stirred again for 5 hours. 20 ml of water were then added, the mixture was extracted three times using 30 ml of methyl tert-butyl ether each time, and the combined organic phases were washed twice with 20 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 (2/1).

Workup

  1. stirringthe mixture was stirred at 80° C. for 6 hours
  2. stirringthe mixture was stirred again for 5 hours
  3. extractionthe mixture was extracted three times
  4. washthe combined organic phases were washed twice with 20 ml of water each time
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, heptane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-d8c634a9f6534d329bcecab2c5f207bf
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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