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

HRID 12083
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12083
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cc6e2af832e647b48d62bc7d748f45c5
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07727986B2

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