(4-Cyclopropyl-6-methoxypyrimidin-5-yl)boronic acid Chemical Properties

Boiling point:

402.1±55.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

pka

2.49±0.58(Predicted)

InChI

InChI=1S/C8H11BN2O3/c1-14-8-6(9(12)13)7(5-2-3-5)10-4-11-8/h4-5,12-13H,2-3H2,1H3

InChIKey

BYXHEUWWJYYRNH-UHFFFAOYSA-N

SMILES

B(C1=C(OC)N=CN=C1C1CC1)(O)O

(4-Cyclopropyl-6-methoxypyrimidin-5-yl)boronic acid Usage And Synthesis

Synthesis

To a stirred solution of 5-bromo-4-cyclopropyl-6-methoxy-pyrimidine in toluene and tetrahydrofuran was added triisopropyl borate at room temperature under nitrogen atmosphere. The mixture was cooled down to -70 °C. To the above mixture was slowly added n-butyl lithium dropwise at -70 °C. The resulting mixture was stirred for additional 15 min at -70 °C. The reaction was quenched with 1N HCl at -70 °C. The mixture was purified by RP-Flash, the collected fractions were combined and concentrated under reduced pressure to afford (4-Cyclopropyl-6-methoxypyrimidin-5-yl)boronic acid (3.5 g, 18.04 mmol, 94% yield) as a white solid.