Ammonium formate → 3-(3-Methylpyridazin-4-yloxy)pyridin-2-amine

HRID 1809645

Reaktionsgleichung

Reaktionsgleichung von HRID 1809645
Cl[C:2]1[N:7]=[N:6][C:5]([CH3:8])=[C:4]([O:9][C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:8][C:5]1[N:6]=[N:7][CH:2]=[CH:3][C:4]=1[O:9][C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 866411083-(6-Chloro-3-methylpyridazin-4-yloxy)pyridin-2-amine

Produkt 1

HCID 674859363-(3-Methylpyridazin-4-yloxy)pyridin-2-amineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3-(6-Chloro-3-methylpyridazin-4-yloxy)pyridin-2-amine (3.0 g, 12.7 mmol) was charged with MeOH (150 mL). Pd/C (0.67 g, 0.63 mmol) was added followed by ammonium formate (2.23 g, 35.5 mmol). The mixture was heated at 65° C. overnight. The solution was cooled and filtered through GF/F paper. The filtrate was concentrated and the residue was dissolved in dichloromethane and saturated NaHCO3. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organics were dried and concentrated to give 3-(3-methylpyridazin-4-yloxy)pyridin-2-amine (1.85 g, 72%) as a solid.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. filtrationfiltered through GF/F paper
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted twice with dichloromethane
  7. customThe combined organics were dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ab8f16fdfeb7404c8cd72867e0bbbefb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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