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

HRID 1809645Notes

Reaction equation

HRID 1809645 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ab8f16fdfeb7404c8cd72867e0bbbefb
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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