Ammonium formate → HCID 11486612, Verbindung

HRID 411291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411291
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][N:21]([CH3:37])[C:22]2[N:31]=[C:30]([NH2:32])[C:29]3[C:24](=[CH:25][C:26]([O:35][CH3:36])=[C:27]([O:33][CH3:34])[CH:28]=3)[N:23]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O.[Pd]>[CH3:34][O:33][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:35][CH3:36])[N:23]=[C:22]([N:21]([CH2:20][C:11]1([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH3:37])[N:31]=[C:30]2[NH2:32]

Komponenten

6

Edukt 2

HCID 2723923Ammonium formateHCID 11294944HCID 11294944, Verbindung

Produkt 1

HCID 11486612HCID 11486612, VerbindungAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of N2-(1-Benzyl-4-phenyl-piperidin-4-ylmethyl)-6,7-dimethoxy-N2-methyl-quinazoline-2,4-diamine 10, (1.3 g) and ammonium formate (2.2 g) in 24 ml methanol and 6 ml water was added 10% Pd-C (250 mg). After stirring under reflux for two hours, the reaction mixture was cooled and filtered through celite®. The filtrate was concentrated to a small volume, made basic with potassium carbonate, and extracted with dichloromethane. The extract was dried over potassium carbonate, filtered, and evaporated. The residue was chromatographed on silica gel to provide 800 mg of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 as a white powder, MS: 407 (M+).

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered through celite®
  4. concentrationThe filtrate was concentrated to a small volume
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over potassium carbonate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cc7fd09e00924a6aba162119c87d9c9f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559153B2

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