Reacción #86457

Ecuación de reacción

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

Rendimiento 32.0%

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

Rendimiento 32.0%

Disolventes

—

Hexanes

EtOAc

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   OtroThe solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   OtroThe resultant reaction mixture
5. 5
   Temperaturawas then refluxed for 6 h
6. 6
   OtroAfter completion of the reaction
7. 7
   Temperaturawas cooled to room temperature
8. 8
   Concentraciónconcentrated under vacuum
9. 9
   Otroto obtain a crude
10. 10
    Otroreaction mixture
11. 11
    OtroThe solid precipitated on addition of ethyl acetate to the crude
12. 12
    Otroreaction mixture
13. 13
    Filtraciónwas filtered
14. 14
    Lavadowashed with ether and pentane

Procedimiento

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]+.

Fuente