Dichloromethane → (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 (0.120 ml) was added via syringe through the septum. The reaction mixture was sparged with N2, then PdCl2(dppf).CH2Cl2 (0.042 g, 0.057 mmol) was added. The septum was then replaced with a Teflon screw valve and the vial was sealed. The reaction mixture was heated at 105° C. in a metal pie block. After 18 h, 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. MS (ESI): m/z=140.0 [M+H]+ HPLC Peak ret. T=0.24 minutes was product (HPLC conditions: Column:Luna C18 4.6×30 mm 3 u A:10:90 H2O:ACN NH4OAc/B:10:90 H2O:ACN NH4OAc; 0%-95% B in 2 min; 4 mL/min flow).

Provenance & Evidence