Water → N-Methyl-N-{[4-(pyrimidin-5-yloxy)phenyl]methyl}amine

HRID 1926713Notes

Reaction equation

HRID 1926713 reaction equation
[N:1]1[CH:6]=[C:5]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:4]=[N:3][CH:2]=1.[CH3:16][NH2:17].[BH4-].[Na+].O>CCO>[CH3:16][NH:17][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 716702454-(Pyrimidin-5-yloxy)benzaldehyde

Product 1

HCID 67131490N-Methyl-N-{[4-(pyrimidin-5-yloxy)phenyl]methyl}amineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Pyrimidin-5-yloxy)benzaldehyde (0.344 g, 1.7 mmol) was stirred with 33% methylamine in EtOH (30 mL) at reflux for 3 hours and then concentrated. The residue was dissolved in MeOH and treated with sodium borohydride (0.195 g, 5.2 mmol) over 1 hour and stirred for a further 1 hour. Water was added and the product was extracted three times with EtOAc. The organic phases were combined, washed with brine, dried and concentrated to give 0.267 g (100%) of product that was used without further purification.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in MeOH
  4. extractionthe product was extracted three times with EtOAc
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7243a4e1c2a48cb9556d0e8afde7766
Source dataset
uspto-grants-2012_05
Patent number
US08183251B2

Reaction notes

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