Reaktion #56848

Reaktionsgleichung

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

hydrogen chloride

p-tolylamine

→

title compound

Ausbeute 53.2%

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

Ausbeute 53.2%

Lösungsmittel

ethanol

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating
2. 2
   Temperaturunder reflux for 3.5 hours
3. 3
   Sonstigethe volatiles were evaporated under reduced pressure
4. 4
   workup.ADDITIONThe residue was treated with 1.0 M hydrochloric acid (10 ml)
5. 5
   FiltrationAfter 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
   Sonstigethe volatiles were evaporated under reduced pressure
10. 10
    workup.STIRRINGthe solid was stirred with water (10 ml) for 15 minutes
11. 11
    Filtrationfiltered

Vorschrift

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).

Quelle