Ethyl Acetate → 6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-amine

HRID 69165

Reaction equation

HRID 69165 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].CCO[C:18]([CH3:20])=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:5][N:4]1[CH:20]=[C:18]([C:5]2[N:4]=[N:3][C:2]([NH2:1])=[CH:7][CH:6]=2)[CH:2]=[N:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 622026836-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-amine

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

3-Amino-6-chloropyridazine (7.76 g, 59.9 mmol) was introduced in a round bottom flask with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-1H-pyrazole (13.1 g, 59.9 mmol) and dissolved in 2-dimethoxyethane (160 mL). An aqueous solution of 2 M Na2CO3 (110 mL, 220 mmol) was added to this mixture and also tetrakis-(triphenylphosphine)-palladium (3.5 g, 2.99 mmol). The RM was refluxed for 26 h under nitrogen. Then was taken up with EtOAc and washed with 1N NaOH and brine. The organic layer was dried over Na2SO4 and the solvent was removed. The residue was triturated with Et2O to afford the title compound as a yellow solid (tR 0.9 min (conditions 2), MH+=176).

Workup

  1. temperatureThe RM was refluxed for 26 h under nitrogen
  2. washwashed with 1N NaOH and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed
  5. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-838935df22194fc2983e290890e65c7f
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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