Ethyl Acetate → (2-Chloropyrimidin-4-yl)quinolin-3-ylamine

HRID 495448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495448
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CCN(C(C)C)C(C)C.CCOC(C)=O>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 113753-AminoquinolineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Produkt 1

HCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol), 3-aminoquinoline (1.1 g, 7.79 mmol) and DIEA (2.0 mL, 11.5 mmol) in IPA (8 mL) was heated to reflux for 48 h. The mixture was poured into EtOAc (200 mL) and washed with H2O (100 mL). The organics were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified via medium pressure liquid chromatography using 50:50 EtOAc/hexanes followed by 100% EtOAc followed by 5:95 MeOH/CH2Cl2 followed by 1.0:10:90 conc. NH4OH/MeOH/CH2Cl2 as the solvent system. (2-Chloropyrimidin-4-yl)-quinolin-3-yl-amine was obtained as a tan solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. washwashed with H2O (100 mL)
  4. dry with materialThe organics were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via medium pressure liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dcd88f54e0b249edb201d535306f0c55
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939874B2

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