2-Amino-1,3-dimethylguanidine hydroiodide → Methyl-(4-methyl-5-pyridin-4-yl4H-[1,2,4]triazol-3-yl)-amine

HRID 732035Notes

Reaction equation

HRID 732035 reaction equation
I.[NH2:2][NH:3][C:4]([NH:7][CH3:8])=[N:5][CH3:6].Cl.[C:10](Cl)(=O)[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:8][NH:7][C:4]1[N:5]([CH3:6])[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:2][N:3]=1

Participants

4

Reactant 2

HCID 122527052-Amino-1,3-dimethylguanidine hydroiodideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 57837980Methyl-(4-methyl-5-pyridin-4-yl4H-[1,2,4]triazol-3-yl)-amineYield 26.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1000 mg (4.35 mmol) N-amino-N′,N″-dimethyl-guanidine hydriodide (Henry; Smith; J.Amer.Chem.Soc.; 73; 1951; 1858) and 774 mg (4.35 mmol) isonicotinoyl chloride hydrochloride in 3 ml of pyridine was heated with microwaves for 5 min at 160° C. K2CO3(sat) was added and the mixture was extracted 4 times with CHCl3. The organic phase was dried and concentrated. Recrystallization from ethanol, water and EtOAc gave 216 mg (26%) of a yellow white solid. 1H NMR (DMSO), d (ppm): 2.85 (d, 3 H) 3.45 (s, 3 H) 6.25 (d, 1 H) 7.65 (m, 2 H) 8.67 (m, 2 H).

Workup

  1. extractionthe mixture was extracted 4 times with CHCl3
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customRecrystallization from ethanol, water and EtOAc

Sources & evidence

ORD record
ord-5af4d9cae5524d95b6ab908e098e85f1
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…