Acetic Acid → 3,5-Dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridine

HRID 2220072Notes

Reaction equation

HRID 2220072 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.CC(O[N:16]=O)(C)C.C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[CH3:9][N:8]1[C:6]2=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=[C:5]2[N:10]=[N:16]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 516892Sodium BicarbonateHCID 22036951N2,6-Dimethylpyridine-2,3-diamine

Product 1

HCID 450794453,5-Dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridineYield 76.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

6,N2-dimethyl-pyridine-2,3-diamine of Step A (1.5 g, 10.9 mmol), 2-methyl-2-nitrosooxy-propane (1.6 ml, 13.1 mmol), acetic acid (2.6 ml, 43.6 mmol), and ethanol (50 ml) were stirred at 60° C. for 60 min. After cooling to ambient temperature, sodium hydrogen carbonate (3 g) was added and the resulting mixture was stirred at ambient temperature for 20 min. The mixture was diluted with dichloromethane (20 ml), solids were filtered off, and the obtained solution was concentrated in vacuum. Chromatography on silica gel, eluting with dichloromethane-acetonitrile (93:7) yielded the title compound (1.23 g, 76%).

Workup

  1. filtrationwere filtered off
  2. concentrationthe obtained solution was concentrated in vacuum
  3. washChromatography on silica gel, eluting with dichloromethane-acetonitrile (93:7)

Sources & evidence

ORD record
ord-e3448136d0034f319c88efeaf03f69a2
Source dataset
uspto-grants-2008_08
Patent number
US07417041B2

Reaction notes

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