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

HRID 12083

반응식

HRID 12083 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc6e2af832e647b48d62bc7d748f45c5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727986B2

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