Water → 4-(2,2-Dimethyl-propylamino)-6-(pyridin-4-ylmethoxy)-quinazoline-2-carbonitrile

HRID 1984229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984229
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1.Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:13]=2)[N:8]=[C:7]([C:16]#[N:17])[N:6]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 686472384-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile

Produkt 1

HCID 686473924-(2,2-Dimethyl-propylamino)-6-(pyridin-4-ylmethoxy)-quinazoline-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(2,2-Dimethyl-propylamino)-6-hydroxy-quinazoline-2-carbonitrile (0.23 mmol), 4-chloromethyl-pyridine hydrochloride (0.35 mmol) and cesium carbonate (2.3 mmol) are stirred in DMF (3 ml) at RT for 20 hours. Water is added until a clear solution is formed. Then more water is added until the solution gets turbide. The precipitate formed is filtered off, washed with water and dried (vacuum). A powder with mp. 203-205° C., Rf=0.2 (CH2Cl2/MeOH=15:1) is obtained. 1H-NMR (CDCl3): 1.0 (m, 9H), 3.55 (m, 2H), 5.2 (m, 2H), 5.8 (broad m, 1H), 7.05 (m, 1H), 7.4 (m, 2H), 7.55 (d, 1H), 7.85 (d, 1H), 8.65 (m, 2H).

Aufarbeitung

  1. customis formed
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried (vacuum)
  6. customA powder with mp. 203-205° C., Rf=0.2 (CH2Cl2/MeOH=15:1) is obtained

Quellen und Nachweise

ORD-Eintrag
ord-62e432a853e6443980f5c5d7140bc01a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544688B2

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