Sodium hydride → 5-[N-(3-bromo-4-fluorobenzyl)-N-(4cyanophenyl)amino]pyrimidine

HRID 1735772

Reaction equation

HRID 1735772 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)=[CH:7][CH:6]=1)#[N:4].[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:22]Br>CN(C)C=O>[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:22][N:11]([C:12]1[CH:17]=[N:16][CH:15]=[N:14][CH:13]=1)[C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 105358714-(Pyrimidin-5-ylamino)benzonitrileHCID 129227103-Bromo-4-fluorobenzyl Bromide

Product 1

HCID 105240055-[N-(3-bromo-4-fluorobenzyl)-N-(4cyanophenyl)amino]pyrimidineYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.04 g of sodium hydride (60% in a mineral oil) in 2 ml of N,N-dimethylformamide was added 0.2 g of 5-[N-(4-cyanophenyl)amino]pyrimidine at room temperature, followed by stirring at that temperature for 1 hour. To the solution was added 0.27 g of 3-bromo-4-fluorobenzyl bromide while cooling with ice, and the mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation under reduced pressure, and water was added to the residue, followed by extraction with chloroform. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to collect crude crystals from the chloroform eluate. The crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethyl ether to obtain 0.25 g of 5-[N-(3-bromo-4-fluorobenzyl)-N-(4cyanophenyl)amino]pyrimidine.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. customThe solvent was removed by distillation under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography
  10. customto collect crude crystals from the chloroform
  11. customThe crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-5dee0cc3cdb74479af6b4498aabb3dd5
Source dataset
uspto-grants-1996_07
Patent number
US05538976

Linked notes

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