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Ammonium formate → 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-one

HRID 843650
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 843650
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:13][C:14]1[N:15]=[C:16]([CH3:19])[S:17][CH:18]=1)[N:6]([C:20]1[C:21]([CH3:26])=[N:22][CH:23]=[CH:24][CH:25]=1)[C:5]2=[O:27].C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][C:14]1[N:15]=[C:16]([CH3:19])[S:17][CH:18]=1)[N:6]([C:20]1[C:21]([CH3:26])=[N:22][CH:23]=[CH:24][CH:25]=1)[C:5]2=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 498262226-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one

Produkt 1

HCID 226116916-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a slurry of 10% palladium on carbon (0.15 g) in methanol(12 mL) were added 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3 H-quinazolin-4-one (0.075 g, 0.198 mmol) and ammonium formate (1.2 g, 19 mmol). The mixture was refluxed overnight, cooled and filtered through celite. The pad was washed with methanol. The filtrate was concentrated. The residue was partitioned between chloroform and water. The phases were separated and the aqueous layer was extracted with chloroform. The combined organic phase was washed with water and brine, dried over magnesium sulfate, and concentrated to afford 0.035 g (47%) of 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-one as a white solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered through celite
  4. washThe pad was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. customThe residue was partitioned between chloroform and water
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with chloroform
  9. washThe combined organic phase was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9cfb6ac370e64f39aadf892d79169351
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06380204B1

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