Reaktion #2469778

Reaktionsgleichung

Intermediate C

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

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

Intermediate B

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

DCM

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

→

title compound

N-[5-(2-Amino-4-methyl-pyrimidin-5-yl)-2-chloro-phenyl]-benzenesulfonamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcontaining
2. 2
   Sonstigedegassed DME (3 ml) and 2M Na2CO3 (1 ml)
3. 3
   TemperaturThe resulting mixture is heated
4. 4
   Sonstigeat 100° C.
5. 5
   Sonstigefor 45 minutes
6. 6
   workup.ADDITIONThe reaction mixture is diluted with DCM, MgSO4
7. 7
   workup.ADDITIONis added
8. 8
   Filtrationthe mixture is filtered through Celite® (filter agent)
9. 9
   SonstigeThe filtrate is absorbed onto silica and purification by flash chromatography on silica eluting with MeOH

Vorschrift

N-[2-Chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (Intermediate B) (50 mg, 0.13 mmol), 5-Bromo-4-methyl-pyrimidin-2-ylamine (Intermediate C) (26 mg, 0.14 mmol) and PdCl2(dppf).DCM (10 mg, 0.013 mmol) are placed in a microwave vial containing degassed DME (3 ml) and 2M Na2CO3 (1 ml). The resulting mixture is heated using microwave radiation at 100° C. for 45 minutes. The reaction mixture is diluted with DCM, MgSO4 is added and the mixture is filtered through Celite® (filter agent). The filtrate is absorbed onto silica and purification by flash chromatography on silica eluting with MeOH:DCM (1% to 2% MeOH) affords the title compound.

Quelle