Sodium hydride → HCID 15819181, compound

HRID 1735750Notes

Reaction equation

HRID 1735750 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]([C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)[CH2:25][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:29])[F:30])=[CH:28][CH:27]=2)=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 107039145-Pyrimidinamine, N-(4-nitrophenyl)-

Product 1

HCID 15819181HCID 15819181, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 40 mg of sodium hydride in 2 ml of N,N-dimethylformamide was added 0.22 g of 5-[(4-nitrophenyl)amino]pyrimidine in small portions. After stirring at room temperature for 30 minutes, 0.24 g of 4-trifluoromethylbenzyl bromide was added thereto, followed by stirring at room temperature for 2 hours. The solvent was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted 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 recover crude crystals from the chloroform eluate. Recrystallization of the crude crystals from a mixed solvent of ethyl acetate and ethyl ether yielded 0.19 g of 5-[N-(4-nitrophenyl)-N-(4trifluoromethylbenzyl)amino]pyrimidine.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography
  9. customto recover crude crystals from the chloroform eluate
  10. customRecrystallization of the crude crystals from a mixed solvent of ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-8894e5fcce6c4c8cb1c574465c60b238
Source dataset
uspto-grants-1996_07
Patent number
US05538976

Reaction notes

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