Potassium Carbonate → 3-amino-6-[(4-propyl-1H-1,2,4-triazol-3-yl)methylthio]pyridazine

HRID 856627Notes

Reaction equation

HRID 856627 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([SH:8])=[CH:6][CH:7]=1.Cl.Cl[CH2:11][C:12]1[N:16]([CH2:17][CH2:18][CH3:19])[CH:15]=[N:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[N:3]=[N:4][C:5]([S:8][CH2:11][C:12]2[N:16]([CH2:17][CH2:18][CH3:19])[CH2:15][NH:14][N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 229387553-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochlorideHCID 1785078036-aminopyridazine-3-thiol

Product 1

HCID 695219413-amino-6-[(4-propyl-1H-1,2,4-triazol-3-yl)methylthio]pyridazineYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-amino-6-mercaptopyridazine (0.5 g), 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride (0.57 g) and potassium carbonate (0.8 g) were added to N,N-dimethylformamide (5 ml), and the mixture was stirred for 4.5 hours at room temperature. The solvent was distilled off, and to the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by basic silica gel column chromatography (elution solvent: methanol/ethyl acetate), to give 3-amino-6-[(4-propyl-1H-1,2,4-triazol-3-yl)methylthio]pyridazine (0.62 g) as colorless crystals.

Workup

  1. distillationThe solvent was distilled off
  2. additionto the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by basic silica gel column chromatography (elution solvent: methanol/ethyl acetate)

Sources & evidence

ORD record
ord-da6c4ee999f64a41aa348d492f6e08fb
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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