Potassium Carbonate → HCID 22007312, compound

HRID 323873Notes

Reaction equation

HRID 323873 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.[O:26]([CH2:33][CH2:34]Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:34][CH2:33][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 6856307-Benzyl-3-methylxanthine

Product 1

HCID 22007312HCID 22007312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.6 g (18.72 mmol) of potassium carbonate were added at 60° C. to a suspension of 3.0 g (11.7 mmol) of 7-benzyl-3-methylxanthine (prepared according to Example 1a) in 70 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 3.1 g (15.21 mmol) of 2-phenoxyethyl bromide were then added dropwise and the mixture was stirred at 80° C. for 5 hours. The crude mixture was then filtered, the filtrate was concentrated under reduced pressure, the residue was taken up in dichloromethane and the solution was washed once with 1 N sodium hydroxide solution and twice with water. The organic phases were 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 (1/2).

Workup

  1. stirringthe mixture was stirred at 80° C. for 5 hours
  2. filtrationThe crude mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washthe solution was washed once with 1 N sodium hydroxide solution and twice with water
  5. customThe organic phases were dried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, heptane/ethyl acetate (1/2)

Sources & evidence

ORD record
ord-5a075d50685c413a97bc0cb1ed8448b1
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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