Water → HCID 22007304, compound

HRID 323877Notes

Reaction equation

HRID 323877 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[C:16]2[N:15]=[CH:14][N:13]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]=2[C:11](=[O:36])[NH:10][C:9]1=[O:37].[Cl:38][C:39]1[CH:49]=[CH:48][C:42]([CH2:43][O:44][CH2:45][CH2:46]Cl)=[CH:41][CH:40]=1.O>CN1CCCC1=O>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:43][O:44][CH2:45][CH2:46][N:10]2[C:11](=[O:36])[C:12]3[N:13]([C:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:14]=[N:15][C:16]=3[N:8]([CH3:7])[C:9]2=[O:37])=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2235351-Chloro-4-[(2-chloroethoxy)methyl]benzene2×HCID 22007310HCID 22007310, compound

Product 1

HCID 22007304HCID 22007304, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.3 g (9.44 mmol) of potassium carbonate were added at 60° C. to a solution of 2.4 g (5.9 mmol) of 3-methyl-7-tritylxanthine (prepared according to Example 17a) in 50 ml of N-methylpyrrolidone and the mixture was stirred at this temperature for one hour. 1.57 g (7.67 mmol) of 2-(4-chlorobenzyloxy)ethyl chloride were then added dropwise and the mixture was stirred at 80° C. for one hour. A further 1.0 g (4.9 mmol) of 2-(4-chlorobenzyloxy)ethyl chloride was then added and the mixture was stirred again for one hour. 50 ml of water were then added, the mixture was extracted three times using 60 ml of methyl tert-butyl ether each time, and 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, heptane/ethyl acetate (3/2).

Workup

  1. stirringthe mixture was stirred at 80° C. for one hour
  2. stirringthe mixture was stirred again for one hour
  3. extractionthe mixture was extracted three times
  4. washthe combined organic phases were washed twice with 30 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 (3/2)

Sources & evidence

ORD record
ord-12e1351a79ff47619b58315c6d38dbef
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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