Reaktion #629097

Reaktionsgleichung

3-aminophenol

potassium carbonate

2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethanol

3-aminophenol

p-toluenesulfonic acid monohydrate

→

desired product

Ausbeute 96.1%

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

Ausbeute 96.1%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 100° C. for 1 h
2. 2
   Extraktionextracted with ethyl acetate (2×50 mL)
3. 3
   WaschenThe combined organic layers were washed with brine (25 mL)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated to a crude brown oil
7. 7
   SonstigeThis material was purified by flash column chromatography

Vorschrift

A solution of 2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethanol (0.10 g, 0.35 mmol) and 3-aminophenol (58 mg, 0.53 mmol) in 1,4-dioxane (3.5 mL) was treated with p-toluenesulfonic acid monohydrate (54 mg, 0.28 mmol) and heated at 100° C. for 1 h. The reaction mixture was treated with additional 3-aminophenol (19 mg, 0.18 mmol) and heated at 100° C. for 1 h. The reaction mixture was poured into 10% potassium carbonate (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude brown oil. This material was purified by flash column chromatography to give the desired product (0.12 g, 96%) as a light brown solid. LCMS for C18H18ClN4O2 (M+H)+: m/z=357.0.

Quelle