Reaktion #86457

Reaktionsgleichung

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

Ausbeute 32.0%

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

Ausbeute 32.0%

Lösungsmittel

—

Hexanes

EtOAc

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   SonstigeThe solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   SonstigeThe resultant reaction mixture
5. 5
   Temperaturwas then refluxed for 6 h
6. 6
   SonstigeAfter completion of the reaction
7. 7
   Temperaturwas cooled to room temperature
8. 8
   Einengenconcentrated under vacuum
9. 9
   Sonstigeto obtain a crude
10. 10
    Sonstigereaction mixture
11. 11
    SonstigeThe solid precipitated on addition of ethyl acetate to the crude
12. 12
    Sonstigereaction mixture
13. 13
    Filtrationwas filtered
14. 14
    Waschenwashed with ether and pentane

Vorschrift

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]+.

Quelle