Reaktion #56817

Reaktionsgleichung

p-tolylamine

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

hydrogen chloride

→

title compound

Ausbeute 98.4%

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

Ausbeute 98.4%

Lösungsmittel

ethanol

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturunder reflux for 75 minutes
3. 3
   SonstigeAfter evaporation of volatiles under reduced pressure
4. 4
   workup.ADDITIONthe residue was treated 1.0 M hydrochloric acid (10 ml)
5. 5
   FiltrationAfter 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
   Sonstigewere evaporated under reduced pressure
10. 10
    workup.ADDITIONThe residue was treated with water (10 ml)
11. 11
    workup.STIRRINGstirred for 15 minutes
12. 12
    FiltrationFiltration

Vorschrift

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).

Quelle