2-Hydrazinopyridine → HCID 87779464, compound

HRID 1946989Notes

Reaction equation

HRID 1946989 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][N:4]=1.[NH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[NH2:12]>CCO>[CH3:1][S:2][C:3]1[N:8]=[C:7](/[CH:9]=[N:12]/[NH:11][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 154070082-Methylsulfanylpyrimidine-4-carbaldehyde

Product 1

HCID 87779464HCID 87779464, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methylsulfanyl-pyrimidine-4-carbaldehyde (1.00 g) (U.S. Pat. No. 6,218,537) and 2-hydrazinopyridine (0.71 g) in EtOH (20 mL) was heated to reflux for 24 h, then cooled to RT and the resulting solid collected by filtration to give N-[1-(2-methylsulfanyl-pyrimidin-4-yl)-meth-(E)-ylidene]-N′-pyridin-2-yl-hydrazine (1.26 g). A mixture of this material and DCM (20 mL) was gently heated, and a second aliquot of DCM (10 mL) and chloroform (5 mL) added to facilitate solubilization. Iodobenzene diacetate (1.65 g) was added, and the resulting mixture stirred at RT under N2 for 17 h. The reaction mixture was then evaporated under reduced pressure and the crude residue was triturated with hot Et2O. Once the mixture cooled to RT, the solid was collected by filtration to afford 3-(2-methylsulfanyl-pyrimidin-4-yl)-[1,2,4]triazolo-[4,3-a]pyridine (1.12 g).

Workup

  1. temperatureto reflux for 24 h
  2. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-da001565cb9044ce86921c0451e7a7f4
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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