Reacción #168890

Ecuación de reacción

2-chloro-4-(phenylthio)pyrimidine

diisopropylethylamine

1,3-phenylenediamine

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product

Rendimiento 42.0%

N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

Rendimiento 42.0%

Disolventes

2-ethoxyethanol

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe whole was heated
2. 2
   Temperaturaunder reflux for 20 hours
3. 3
   Lavadowashed with water and brine
4. 4
   SecadoThe organic solution was dried (Na2SO4)
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otrochromatographed on silica gel

Procedimiento

To a stirred mixture of 2-chloro-4-(phenylthio)pyrimidine (300 mg, 1.35 mmol) and diisopropylethylamine (0.35 mL, 2.02 mmol) in 2-ethoxyethanol (2 mL), was added 1,3-phenylenediamine (291 mg, 2.70 mmol) in one portion. The whole was heated under reflux for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), washed with water and brine. The organic solution was dried (Na2SO4), concentrated in vacuo. The residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (20:80→0:50) as eluant to give the product (167 mg, 42%).

Fuente