반응 #1702113

반응 방정식

NaHCO3

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2-(3-aminophenyl)ethanol

p-toluenesulfonic acid monohydrate

→

desired product

수율 74.0%

2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol

수율 74.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   기타The organic solvent was removed under vacuum
2. 2
   workup.ADDITIONfollowed by the addition of water and EtOAc
3. 3
   추출The aqueous layer was extracted with EtOAc twice
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated under vacuum
6. 6
   기타The crude was purified by silica gel column chromatography

실험 절차

Into a reaction flask were added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.33 g, 1.2 mmol) (prepared according to Example 1, step A), 1,4-dioxane (20 mL), 2-(3-aminophenyl)ethanol (0.22 g, 1.6 mmol), and p-toluenesulfonic acid monohydrate (0.080 g, 0.42 mmol). The mixture was heated at 105° C. for 3 hours and then an aqueous solution of NaHCO3 (saturated) was added. The organic solvent was removed under vacuum followed by the addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, and concentrated under vacuum. The crude was purified by silica gel column chromatography to provide the desired product as a white solid (0.33 g, 74% yield). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

출처