Methylamine → N-Methyl-N-[(4-{[2-(trifluoromethyl)pyrimidin-5-yl]oxy}phenyl)methyl]amine

HRID 1926719Notes

Reaction equation

HRID 1926719 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[CH:5][N:4]=1.[CH3:20][NH2:21]>C(O)C>[CH3:20][NH:21][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([O:9][C:6]2[CH:5]=[N:4][C:3]([C:2]([F:19])([F:18])[F:1])=[N:8][CH:7]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 866231314-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}benzaldehyde

Product 1

HCID 67131360N-Methyl-N-[(4-{[2-(trifluoromethyl)pyrimidin-5-yl]oxy}phenyl)methyl]amineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-{[2-(Trifluoromethyl)pyrimidin-5-yl]oxy}benzaldehyde was stirred with 33% methylamine in 95% ethanol (30 mL) at reflux for 1 hour and then concentrated. The residue was re-dissolved in 95% ethanol, 10% palladium/carbon was added, and the mixture was hydrogenated at room temperature under atmospheric pressure for 30 minutes. The reaction was performed on a 5.0 mmol scale with a yield of 95%.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationconcentrated
  3. dissolutionThe residue was re-dissolved in 95% ethanol
  4. addition10% palladium/carbon was added

Sources & evidence

ORD record
ord-d96ceca2f1704177a97dbbdacbd3f42b
Source dataset
uspto-grants-2012_05
Patent number
US08183251B2

Reaction notes

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