Reacción #56817

Ecuación de reacción

p-tolylamine

4-chloro-6-(5-chloro-2-methyl-phenyl)-pyrimidin-2-yl-amine

hydrogen chloride

→

title compound

Rendimiento 98.4%

6-(5-Chloro-2-methyl-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine

Rendimiento 98.4%

Disolventes

ethanol

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaunder reflux for 75 minutes
3. 3
   OtroAfter evaporation of volatiles under reduced pressure
4. 4
   workup.ADDITIONthe residue was treated 1.0 M hydrochloric acid (10 ml)
5. 5
   FiltraciónAfter filtration the solid
6. 6
   workup.DISSOLUTIONwas dissolved in methanol (5 ml)
7. 7
   workup.ADDITIONtreated with a solution of sodium carbonate in water (1.0 M, 1.0 ml)
8. 8
   workup.STIRRINGAfter stirring for 30 minutes volatiles
9. 9
   Otrowere evaporated under reduced pressure
10. 10
    workup.ADDITIONThe residue was treated with water (10 ml)
11. 11
    workup.STIRRINGstirred for 15 minutes
12. 12
    FiltraciónFiltration

Procedimiento

To a stirred suspension of the hydrochloride salt of 4-chloro-6-(5-chloro-2-methyl-phenyl)-pyrimidin-2-yl-amine (0.01 g, 0.0344 mmol) in ethanol (5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.01 ml) followed by p-tolylamine (0.074 g, 0.068 mmol). The mixture was heated under reflux for 75 minutes. After evaporation of volatiles under reduced pressure, the residue was treated 1.0 M hydrochloric acid (10 ml) and stirred for 30 minutes. After filtration the solid was dissolved in methanol (5 ml) and treated with a solution of sodium carbonate in water (1.0 M, 1.0 ml). After stirring for 30 minutes volatiles were evaporated under reduced pressure. The residue was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.011 g, 98% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.27 (s, 3H, CH3), 2.34 (s, 3H, CH3), 6.07 (s, 1H, Ar), 6.33 (s, 2H, NH2), 7.10 (d, 2H, J=8.3 Hz, Ar), 7.30 (d, 1H, J=8.2 Hz, Ar), 7.35-7.40 (m, 2H, Ar), 7.61 (d, 1H, J=8.4 Hz, Ar), 9.09 (s, 1H, NH).

Fuente