Reaktion #2469783

Reaktionsgleichung

DCM

2-chloro-N-(4-hydroxy-cyclohexyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide

2-Chloro-N-(4-hydroxy-cyclohexyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide

5-Bromo-4 methyl-pyrimidin-2-ylamine

5-Bromo-4-methyl-pyrimidin-2-ylamine

intermediate C

5-Bromo-4-methyl-pyrimidin-2-ylamine

→

title compound

5-(2-Amino-4-methyl-pyrimidin-5-yl)-2-chloro-N-(4-hydroxy-cyclohexyl)-Benzenesulfonamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcontaining
2. 2
   Sonstigedegassed DME (10 ml) and 2M Na2CO3 (2 ml)
3. 3
   TemperaturThe resulting mixture is heated
4. 4
   Sonstigeat 100° C.
5. 5
   Sonstigefor 15 minutes
6. 6
   SonstigeAfter evaporation of the solvent
7. 7
   Sonstigethe reaction mixture is purified by flash chromatography on silica eluting with ethanol

Vorschrift

The crude 2-chloro-N-(4-hydroxy-cyclohexyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide from step 2 (1.48 g), 5-Bromo-4 methyl-pyrimidin-2-ylamine (intermediate C) (0.669 g, 3.36 mmol) and PdCl2(dppf).DCM (0.436 g, 0.53 mmol) are placed in a microwave vial containing degassed DME (10 ml) and 2M Na2CO3 (2 ml). The resulting mixture is heated using microwave radiation at 100° C. for 15 minutes. After evaporation of the solvent, the reaction mixture is purified by flash chromatography on silica eluting with ethanol to afford the title compound.

Quelle