Reacción #56848

Ecuación de reacción

4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

hydrogen chloride

p-tolylamine

→

title compound

Rendimiento 53.2%

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

Rendimiento 53.2%

Disolventes

ethanol

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating
2. 2
   Temperaturaunder reflux for 3.5 hours
3. 3
   Otrothe volatiles were evaporated under reduced pressure
4. 4
   workup.ADDITIONThe residue was treated with 1.0 M hydrochloric acid (10 ml)
5. 5
   FiltraciónAfter filtration
6. 6
   workup.DISSOLUTIONthe solid was dissolved in methanol (10 ml)
7. 7
   workup.ADDITIONtreated with aqueous sodium carbonate solution (1.0 M, 1 ml)
8. 8
   workup.STIRRINGAfter stirring for 0.5 hours
9. 9
   Otrothe volatiles were evaporated under reduced pressure
10. 10
    workup.STIRRINGthe solid was stirred with water (10 ml) for 15 minutes
11. 11
    Filtraciónfiltered

Procedimiento

To a stirred suspension of 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.030 g, 0.106 mmol) in ethanol (5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.015 ml) followed by p-tolylamine (0.014 g, 0.127 mmol). After heating under reflux for 3.5 hours, the volatiles were evaporated under reduced pressure. The residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred overnight. After filtration, the solid was dissolved in methanol (10 ml) and treated with aqueous sodium carbonate solution (1.0 M, 1 ml). After stirring for 0.5 hours, the volatiles were evaporated under reduced pressure, the solid was stirred with water (10 ml) for 15 minutes, and filtered to provide the title compound (0.020 g, 53% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.37 (t, 3H, J=6.8 Hz, CH3), 2.27 (s, 3H, CH3), 4.12 (q, 2H, J=6.6 Hz, CH2), 6.25 (s, 2H, NH2), 6.75 (s, 1H, Ar), 7.10-7.14 (m, 3H, Ar), 7.40-7.42 (m, 1H, Ar), 7.55 (d, 2H, J=8.0 Hz, Ar), 7.92 (s, 1H, Ar), 9.05 (s, 1H, NH).

Fuente