Reaction #70340

Reaction equation

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

Solvents

toluene water

water

Conditions

Workup

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

Procedure

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).

Source