تفاعل #1702113

معادلة التفاعل

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

المردود 74.0%

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

المردود 74.0%

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر