Dimethylformamide → HCID 23070724, compound

HRID 501386Notes

Reaction equation

HRID 501386 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[NH:11][C:10]([Cl:15])=[N:9][C:8]=2[N:7]=[C:6]1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)[C:2]#[C:3][CH3:4].[C:29]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)#[N:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C.CCCCCC>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[C:29]#[N:30])[C:10]([Cl:15])=[N:9][C:8]=2[N:7]=[C:6]1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 135829587HCID 135829587, compound

Product 1

HCID 23070724HCID 23070724, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture consisting of 100 mg of t-butyl 4-[7-(2-butynyl)-2-chloro-6-oxo-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate, 60 mg of 2-cyanobenzyl bromide, 68 mg of anhydrous potassium carbonate, and 1 ml of N,N-dimethylformamide was stirred at room temperature for 4 hours. Ethyl acetate/hexane (1/1) and water were added to the reaction solution. The insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 30 to 50% ethyl acetate/hexane to give 50 mg of the title compound.

Workup

  1. customThe insoluble material was removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-10340dc7194a4e948d997d7a2faa5847
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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