Réaction #1572841

Équation de réaction

tert-butyl 4-((4-((3-chloro-4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

potassium carbonate

1,3-dibromopropane

→

tert-butyl 4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

Rendement 78.0%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   AutreTo a dry 30 mL vial equipped with a stir bar
2. 2
   Autrewas placed in a 60° C.
3. 3
   Températureheating block
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

To a dry 30 mL vial equipped with a stir bar was added tert-butyl 4-((4-((3-chloro-4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate (1.80 g, 3.18 mmol), potassium carbonate (1.32 g, 9.55 mmol) and acetone (16 mL). To the mixture was added 1,3-dibromopropane (3.37 ml, 25.5 mmol). The vial was placed in a 60° C. heating block with stirring for 2.5 h. The mixture was cooled to room temperature and then concentrated in vacuo. The resulting solid residue was subjected to SiO2 chromatography (hexanes:EtOAc 85:15 to 75:25) to afford tert-butyl 4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate as a colorless solid (1.60 g, 78%). MS m/z=646.25 (M+H)+.

Source