반응 #317530

반응 방정식

tris(2-methylphenyl)phosphine

2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester

N-(4-iodophenyl)-N-isopropylpyrimidin-2-amine

potassium carbonate

→

(E)-2-(2,6-dichlorobenzamido)-5-[4-(isopropyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester

수율 66.9%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   온도After cooling the reaction solution to room temperature
2. 2
   세척the resulting mixture was washed twice with water and once with saturated brine
3. 3
   건조by drying the organic layers over anhydrous sodium sulfate
4. 4
   기타After removing anhydrous sodium sulfate
5. 5
   여과by filtration
6. 6
   농축the filtrate was concentrated
7. 7
   기타The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/2)
8. 8
   기타The obtained crudely purified product
9. 9
   기타was purified again by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1→4/1)

실험 절차

Under an argon atmosphere, palladium acetate (316.7 mg) and tris(2-methylphenyl)phosphine (411.8 mg) were added to a suspension of 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (4.09 g), N-(4-iodophenyl)-N-isopropylpyrimidin-2-amine (4.59 g) and potassium carbonate (2.80 g) in DMF (50 ml), and the resulting mixture was stirred at 80° C. for 6 hours. After cooling the reaction solution to room temperature, ethyl acetate was added thereto and the resulting mixture was washed twice with water and once with saturated brine, followed by drying the organic layers over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/2). The obtained crudely purified product was purified again by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1→4/1) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(isopropyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (4.65 g).

출처