Potassium Acetate → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

3-(5-Chloropyrimidin-2-yl)propanoate (1.49 g, 6.97 mmol), bis(pinacolato)diboron (1.95 g, 7.67 mmol), and potassium acetate (1.1 g, 11.15 mmol) were suspended in dioxane (34.8 mL). The system was evacuated and then purged with Ar three times before adding bis(tricyclohexylphosphine)palladium(0) (0.12 g, 0.17 mmol). The system was evacuated and then purged with Ar three times before capping and heating the mixture to 85° C. for 16 hours. The reaction was allowed to cool to room temperature, filtered through CELITE, and concentrated in vacuo. The residue was purified by reverse phase column chromatography using a C18 column eluting with 3:97 to 100:0 acetonitrile:water with 0.1% ammonium hydroxide to give [2-(3-ethoxy-3-oxopropyl)pyrimidin-5-yl]boronic acid. MS ESI calcd for C9H14BN2O4 [M+H]+ 225. found 225. 1H NMR (500 MHz, DMSO-d6) δ 8.89 (s, 1H), 8.52 (s, 1H), 4.00 (q, J=7.1 Hz, 2H), 3.12 (t, J=7.0 Hz, 2H), 2.78 (t, J=7.0 Hz, 2H), 1.11 (t, J=7.1 Hz, 3H).

Provenance & Evidence