Water → N4-Quinolin-3-yl-N2-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine

HRID 495451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495451
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[NH2:24].O.C([O-])(O)=O.[Na+]>CC(C)=O.Cl.CCOC(C)=O>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][C:23]3[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:21]([O:20][CH3:19])[CH:22]=3)[N:7]=2)[CH:10]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 322853,4,5-TrimethoxyanilineHCID 516892Sodium BicarbonateHCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

Produkt 1

HCID 10179293N4-Quinolin-3-yl-N2-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (100 mg, 0.39 mmol) and 3,4,5-trimethoxyaniline was suspended in acetone (7 mL) and water (2 mL) with 2 drops of conc. HCl. The mixture was heated in a sealed tube to reflux overnight. The mixture was poured into EtOAc (100 mL) and sat. aq. NaHCO3. The organics were separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified via preparative HPLC. MS m/z=404. Calc'd for C22H21N5O3: 403.16.

Aufarbeitung

  1. temperatureThe mixture was heated in a sealed tube
  2. temperatureto reflux overnight
  3. customThe organics were separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5283f8ad221f460b8724247eeece4653
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939874B2

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