Chloropyrazine → Pyrazin-2-yl-(6-trifluoromethyl-pyridin-3-yl)-amine

HRID 76081Notes

Reaction equation

HRID 76081 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.Cl[C:13]1[CH:18]=[N:17][CH:16]=[CH:15][N:14]=1>C1(C)C=CC=CC=1>[N:14]1[CH:15]=[CH:16][N:17]=[CH:18][C:13]=1[NH:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73277ChloropyrazineHCID 27377445-Amino-2-(trifluoromethyl)pyridine

Product 1

HCID 66615925Pyrazin-2-yl-(6-trifluoromethyl-pyridin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 5-amino-2-trifluoromethylpyridine (0.81 g) in 3 Ml toluene was added chloropyrazine (0.45 Ml, 1.0 equiv) via syringe. The homogeneous solution was heated to 95° C., then cooled to room temperature and concentrated in vacuo. Purification by silica gel chromatography (40% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 7.5 (s, 1H) 7.6 (s, 1H) 8.0 (s, 1H) 8.2 (s, 1H) 8.4 (s, 2H) 8.8 (s, 1H); (M+H)+241.1.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customPurification by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-05ccb44a87384efd87e49f2df85e767d
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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