N-Methylaniline → [4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine

HRID 12083

Reaction equation

HRID 12083 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([NH2:16])=[C:11]([CH3:17])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>Cl>[NH2:16][C:12]1[C:11]([CH3:17])=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:19]([CH3:18])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:7]=2)=[C:14]([CH3:15])[CH:13]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8857Ethyl AcetateHCID 866289744-(2-Chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine

Product 1

HCID 67026468[4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2.50 g (10 mmol) 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine and 2.14 g N-methylaniline (20 mmol) in 50 ml hydrochloric acid were stirred for 20 h at 80° C. After cooling down to ambient temperature 50 ml ethyl acetate was added and the organic layer was separated. The water layer was brought to pH 8 with sodium carbonate and the formed precipitate was filtered by suction and washed with hexane. After separation the organic layer was concentrated in vacuo and column chromatography (dichloromethane) yielded 380 mg (11%) with a purity of 89% log P (pH=2.3)=1.72.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. filtrationthe formed precipitate was filtered by suction
  4. washwashed with hexane
  5. customAfter separation the organic layer
  6. concentrationwas concentrated in vacuo and column chromatography (dichloromethane)
  7. customyielded 380 mg (11%) with a purity of 89% log P (pH=2.3)=1.72

Sources & evidence

ORD record
ord-cc6e2af832e647b48d62bc7d748f45c5
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Linked notes

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