Diethyl Ether → 4-[4-Amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-ylamino]-benzaldehyde

HRID 1591636

Reaktionsgleichung

Reaktionsgleichung von HRID 1591636
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=2)[N:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+:30]1C=CC=CC=1.C(OCC)C>ClCCl>[NH2:30][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 86588970{4-[4-Chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-ylamino]-phenyl}-methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 102909894-[4-Amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-ylamino]-benzaldehydeAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of the title compound of Example 41 (375 mg, 1.1 mmol) in dichloromethane (100 ml) was added pyridinium chlorochromate (810 mg, 2.7 mmol) and crushed molecular sieves (1.25 g, 3A). After stirring for 6 hours, diethyl ether (150 ml) was added and the mixture was filtered through a pad of silica gel under suction. The filtrate was concentrated under reduced pressure and purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2 followed by 1:1) to provide the title compound (25 mg, 7% yield). 1H NMR (DMSO-d6) 10.10 (s, 1H), 9.86 (s, 1H), 8.07 (d, J=8.6 Hz, 2H), 7.84 (d, J=8.6 Hz, 2H), 7.79 (s, 1H), 7.43 (m, 2H), 7.34 (m, 2H), 2.53 (s, 3H).

Aufarbeitung

  1. filtrationthe mixture was filtered through a pad of silica gel under suction
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2 followed by 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-418d5940bbaf431e86f5c8a5fef4f1b9
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291616B2

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