反応 #86457

反応方程式

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

収率 32.0%

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

収率 32.0%

溶媒

—

Hexanes

EtOAc

dioxane

反応条件

後処理

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

実験手順

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]+.

出典