반응 #86457

반응 방정식

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

수율 32.0%

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

수율 32.0%

용매

—

Hexanes

EtOAc

dioxane

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   기타The solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   기타The resultant reaction mixture
5. 5
   온도was then refluxed for 6 h
6. 6
   기타After completion of the reaction
7. 7
   온도was cooled to room temperature
8. 8
   농축concentrated under vacuum
9. 9
   기타to obtain a crude
10. 10
    기타reaction mixture
11. 11
    기타The solid precipitated on addition of ethyl acetate to the crude
12. 12
    기타reaction mixture
13. 13
    여과was filtered
14. 14
    세척washed with ether and pentane

실험 절차

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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