2-(trifluoroMethyl)pyriMidin-5-ylboronic acid Chemical Properties

Boiling point:

236.7±50.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

4.46±0.11(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C5H4BF3N2O2/c7-5(8,9)4-10-1-3(2-11-4)6(12)13/h1-2,12-13H

InChIKey

OEZMIKKBMMAABO-UHFFFAOYSA-N

SMILES

B(C1=CN=C(C(F)(F)F)N=C1)(O)O

2-(trifluoroMethyl)pyriMidin-5-ylboronic acid Usage And Synthesis

Synthesis

To a hexane solution of 0.5 M n-butyllithium (1.7 mL, 2.4 mmol) was added slowly and dropwise a tetrahydrofuran (THF, 10 mL) solution of 5-bromo-2-trifluoromethylpyrimidine (700.6 mg, 3.1 mmol) and triisopropyl borate (1.1 mL, 4.7 mmol) at -78°C. The reaction mixture was stirred continuously at -78 °C for 2 h. The reaction was subsequently quenched with water. The solvent was removed by distillation under reduced pressure and the residue was extracted with ether (2 x 40 mL). After separation of the aqueous layer, the pH was adjusted to 6 with 1N hydrochloric acid and extracted with ethyl acetate (EA, 3 x 40 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated to obtain the target product 2-(trifluoromethyl)pyrimidin-5-ylboronic acid (400 mg, 67.2% yield) as a white solid. Liquid chromatography-mass spectrometry (LC-MS) analysis showed a retention time of 0.66 min and a molecular ion peak (MH+) of 193.

References

[1] Patent: WO2016/44792, 2016, A1. Location in patent: Page/Page column 105; 106