Potassium Acetate → (4-Aminopyrimidin-5-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a vial was added 5-bromopyrimidin-4-amine (0.200 g, 1.149 mmol), bis(pinacolato)diboron (0.438 g, 1.724 mmol), and potassium acetate (0.338 g, 3.45 mmol). The vial was capped with a rubber septum and then evacuated and backfilled with N2. Dioxane (volume: 0.120 ml) was added via syringe through the septum. The reaction mixture was sparged with N2, then 1,1′-bis(diphenylphosphino) ferrocenedichloropalladium(II) dichloromethane complex (0.042 g, 0.057 mmol) was added. The septum was then replaced with a Teflon screw valve and the vial sealed. The reaction mixture was heated at 105° C. in a metal pie block. After 18 h, the reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with EtOAc. The filtrate was concentrated to afford a brown solid. The crude material was used without further purification. MS (ESI): m/z=140.0 [M+H]+. HPLC Peak tr=0.24 minutes. HPLC conditions: Column:Luna C18 4.6×30 mm 3u A:10:90 H2O:ACN NH4OAc/B:10:90 H2O:ACN NH4OAc; 0%-95% B in 2 min; 4 mL/min flow.

Provenance & Evidence