反应 #86457

反应方程式

N4-(4-(2-methoxyethoxy)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamine

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

收率 32.0%

3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(6-((4-(2-methoxyethoxy)-2-nitrophenyl)amino)pyrimidin-4-yl)-1-methylurea

收率 32.0%

溶剂

—

Hexanes

EtOAc

dioxane

反应条件

后处理

1. 1
   温度to cool to room temperature
2. 2
   其他The solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   其他The resultant reaction mixture
5. 5
   温度was then refluxed for 6 h
6. 6
   其他After completion of the reaction
7. 7
   温度was cooled to room temperature
8. 8
   浓缩concentrated under vacuum
9. 9
   其他to obtain a crude
10. 10
    其他reaction mixture
11. 11
    其他The solid precipitated on addition of ethyl acetate to the crude
12. 12
    其他reaction mixture
13. 13
    过滤was filtered
14. 14
    洗涤washed with ether and pentane

实验过程

To a stirred solution of 2,6-dichloro-3,5-dimethoxyaniline (500 g, 2.252 mmol) in dioxane (10 mL) was added 20% phosgene in toluene (4.4 mL, 9.0 mmol) under argon atmosphere at 0° C. The resulting mixture was stirred for 6 h at 90° C., and then allowed to cool to room temperature. The solvents were removed and the residue was dissolved in toluene (10 mL). To this, was added N4-(4-(2-methoxyethoxy)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamine (0.718 g, 8.358 mmol, 1.0 eq). The resultant reaction mixture was then refluxed for 6 h. After completion of the reaction by TLC (Hexanes:EtOAc, 7:3), reaction mixture was cooled to room temperature, concentrated under vacuum to obtain a crude reaction mixture. The solid precipitated on addition of ethyl acetate to the crude reaction mixture was filtered, washed with ether and pentane to afford the title compound (0.285, yield: 32%) as a white solid. MS (ESI): 567.0 [M+H]+.

来源