Reaktion #1702113

Reaktionsgleichung

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

Ausbeute 74.0%

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

Ausbeute 74.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle