تفاعل #86457

معادلة التفاعل

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

2,6-dichloro-3,5-dimethoxyaniline

phosgene

toluene

→

title compound

المردود 32.0%

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

المردود 32.0%

المذيبات

—

Hexanes

EtOAc

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to room temperature
2. 2
   أخرىThe solvents were removed
3. 3
   workup.DISSOLUTIONthe residue was dissolved in toluene (10 mL)
4. 4
   أخرىThe resultant reaction mixture
5. 5
   درجة الحرارةwas then refluxed for 6 h
6. 6
   أخرىAfter completion of the reaction
7. 7
   درجة الحرارةwas cooled to room temperature
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىto obtain a crude
10. 10
    أخرىreaction mixture
11. 11
    أخرىThe solid precipitated on addition of ethyl acetate to the crude
12. 12
    أخرىreaction mixture
13. 13
    ترشيحwas filtered
14. 14
    غسيلwashed with ether and pentane

الإجراء التجريبي

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]+.

المصدر