2-PYRIDINEACETALDEHYDE, ALPHA-OXO- → HCID 43134555, compound

HRID 2407092Notes

Reaction equation

HRID 2407092 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH:9]=O)=O.C(=O)(O)O.[NH2:15][NH:16][C:17]([NH2:19])=[NH:18]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:18]=[C:17]([NH2:19])[N:16]=[N:15][CH:9]=1

Participants

4

Reactant 2

HCID 109535652-PYRIDINEACETALDEHYDE, ALPHA-OXO-HCID 178513185HCID 178513185, compound

Product 1

HCID 43134555HCID 43134555, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(Pyridin-2-yl)-1,2,4-triazin-3-amine (1.5 g, 8% over 2 steps) was prepared from a crude sample of 2-pyridylglyoxal (8.0 g) and aminoguanidine hydrogen carbonate (6.0 g, 44 mmol). The reagents were refluxed in EtOH (100 mL) for 4 hours. The reaction mixture was then cooled, concentrated under reduced pressure and purified by gradient flash chromatography (eluting with 0-30% ethyl acetate/hexane). The sample contained a mixture of isomers at this stage and was used without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated under reduced pressure
  3. custompurified by gradient flash chromatography (eluting with 0-30% ethyl acetate/hexane)
  4. additiona mixture of isomers at this stage
  5. customwas used without further purification

Sources & evidence

ORD record
ord-2d9fa00dc1724e5484d803921c692e45
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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