反应 #56848

反应方程式

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

hydrogen chloride

p-tolylamine

→

title compound

收率 53.2%

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

收率 53.2%

溶剂

ethanol

dioxane

反应条件

后处理

1. 1
   温度After heating
2. 2
   温度under reflux for 3.5 hours
3. 3
   其他the volatiles were evaporated under reduced pressure
4. 4
   workup.ADDITIONThe residue was treated with 1.0 M hydrochloric acid (10 ml)
5. 5
   过滤After 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
   其他the volatiles were evaporated under reduced pressure
10. 10
    workup.STIRRINGthe solid was stirred with water (10 ml) for 15 minutes
11. 11
    过滤filtered

实验过程

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).

来源