Potassium Carbonate → 3-Amino-6-[(3-propylimidazol-4-yl)methylthio]pyridazine

HRID 856628Notes

Reaction equation

HRID 856628 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:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[N:15][CH:16]=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:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[N:15][CH:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 1785078036-aminopyridazine-3-thiol

Product 1

HCID 695227193-Amino-6-[(3-propylimidazol-4-yl)methylthio]pyridazineYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-amino-6-mercaptopyridazine (0.5 g), 4-chloromethyl-3-propylimidazole hydrochloride (0.62 g) and potassium carbonate (2.0 g) were added to N,N-dimethylformamide (10 ml), and the mixture was stirred overnight at room temperature. 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-[(3-propylimidazol-4-yl)methylthio]pyridazine (0.52 g) as yellow crystals.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by basic silica gel column chromatography (elution solvent: methanol/ethyl acetate)

Sources & evidence

ORD record
ord-326aa6da01b9404dbd49eeb93e9415a8
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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