Reaktion #70340

Reaktionsgleichung

2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid

cyclopropylboronic acid

K3PO4

PCy3

→

5-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid

Lösungsmittel

toluene water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   TrocknenThe organic phase was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Sonstigethe solvent removed
5. 5
   SonstigeThe crude mixture was purified by reverse phase chromatography
6. 6
   Wascheneluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield)

Vorschrift

In a schlenck tube, a mixture of 2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid (0.55 mmol, 0.200 g), cyclopropylboronic acid (0.71 mmol, 0.061 g), K3PO4 (1.86 mmol, 0.395 g), PCy3 (0.05 mmol, 0.015 g) and Pd(AcO)2 (0.03 mmol, 0.006 g) in a mixture of toluene/water 6:1 (6 ml) was heated at 110° C. for 72 hours, under argon atmosphere. The crude mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and the solvent removed. The crude mixture was purified by reverse phase chromatography eluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield).

Quelle