Реакция #86457

Уравнение реакции

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

Выход 32.0%

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

Выход 32.0%

Растворители

—

Hexanes

EtOAc

dioxane

Условия реакции

Обработка

1. 1
   Температураto cool to room temperature
2. 2
   ДругоеThe solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   ДругоеThe resultant reaction mixture
5. 5
   Температураwas then refluxed for 6 h
6. 6
   ДругоеAfter completion of the reaction
7. 7
   Температураwas cooled to room temperature
8. 8
   Концентрированиеconcentrated under vacuum
9. 9
   Другоеto obtain a crude
10. 10
    Другоеreaction mixture
11. 11
    ДругоеThe solid precipitated on addition of ethyl acetate to the crude
12. 12
    Другоеreaction mixture
13. 13
    Фильтрацияwas filtered
14. 14
    Промывкаwashed with ether and pentane

Методика

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]+.

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