Hydrochloric Acid → N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine

HRID 1802204Notes

Reaction equation

HRID 1802204 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[N:19]=[C:6]2[CH:7]=[C:8]([NH:11]C(=O)OC(C)(C)C)[CH:9]=[CH:10][N:5]2[N:4]=1.Cl>ClCCl>[CH3:1][N:2]([CH3:20])[C:3]1[N:19]=[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][N:5]2[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67775938HCID 67775938, compound

Product 1

HCID 67774846N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamineYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (1.8 g, 6.49 mmol) in dichloromethane (15 ml) and hydrochloric acid (5N in diethyl ether, 50 ml, 250 mmol) is stirred for 18 hours at room temperature. The solvent is evaporated and the residue dissolved in water (100 ml), made basic with 32% aqueous sodium hydroxide and extracted twice with ethyl acetate. The combined organic layers are washed with water, dried with magnesium sulfate and the solvent is evaporated under reduced pressure affording N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine (727 mg, 63.2%) as a yellow solid. Mp.: 236-8° C. MS: m/z=178.1 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in water (100 ml)
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers are washed with water
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e815509e6e9d458185dc035b73cb0a66
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

Loading…