Ethyl Acetate → 5-amino-2-methyl-N-(pyrimidin-5-yl)benzamide

HRID 2355096

Reaktionsgleichung

Reaktionsgleichung von HRID 2355096
CCOC(C)=O.[CH3:7][C:8]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1)=[O:11].[H][H]>CO.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:8]([CH3:7])=[C:9]([CH:19]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][CH:16]=[N:15][CH:14]=1)=[O:11]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 248232552-methyl-5-nitro-N-(pyrimidin-5-yl)benzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 248240475-amino-2-methyl-N-(pyrimidin-5-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A 2 L high-pressure vessel was charged with Palladium 10% on carbon wet (50% water) and EtOAc (50 mL). 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide 45 (18.79 g) was dissolved in methanol (400 mL) and added to the previous mixture. The reaction vessel was pressurized to 30 psi of H2 and mechanically stirred until the hydrogen intake stopped. The reduction of the nitro group was complete by LCMS and the mixture was filtered off through paper and glass paper. The crude 5-amino-2-methyl-N-(pyrimidin-5-yl)benzamide 46 was obtained as a yellow solid and used without further purification.

Aufarbeitung

  1. additionadded to the previous mixture
  2. filtrationthe mixture was filtered off through paper and glass paper

Quellen und Nachweise

ORD-Eintrag
ord-cf248572e410495aab32c2cbe1551cb3
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754717B2

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