Réaction #162635

Équation de réaction

8,8′-(2,5-dichloropyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane)

ethanol

4-aminophenylboronic acid pinacol ester

sodium carbonate

→

title compound

Rendement 61.3%

4-(5-chloro-4,6-di-3-oxa-8-azabicyclo[3.2.1]oct-8-ylpyrimidin-2-yl)aniline

Rendement 61.3%

Solvants

water

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed under nitrogen overnight
2. 2
   TempératureThe reaction was cooled
3. 3
   Extractionthe mixture was extracted 3 times with ethyl acetate
4. 4
   AutreThe organics were separated
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Filtrationfiltered through Magnesol™
7. 7
   Concentrationconcentrated in vacuo to an oil
8. 8
   AutreThe crude product was purified via silica gel column with hexanes/ethyl acetate

Mode opératoire

To a solution of 8,8′-(2,5-dichloropyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane) (1.0 g, 2.7 mmol) in 1:1 ethanol:toluene (10 mL) was added 4-aminophenylboronic acid pinacol ester (0.7 g, 3.2 mmol), 2.0M solution of sodium carbonate (1.2 mL) and tetrakis(triphenylphosphine) palladium (0) (0.3 g, 10 mol %). The reaction was refluxed under nitrogen overnight. The reaction was cooled and water was added (75 mL) and the mixture was extracted 3 times with ethyl acetate. The organics were separated and dried over magnesium sulfate, then filtered through Magnesol™ and concentrated in vacuo to an oil. The crude product was purified via silica gel column with hexanes/ethyl acetate to yield the title compound as a white solid (0.708 g). MS m/z=428 (M+H).

Source