Cesium carbonate → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-3-yl-pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (268 mg, 0.81 mmol), 3-pyridyl boronic acid (1.84 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), (t-Bu)3P (8 mg, 0.04 mmol) and Cs2CO3 (600 mg, 1.84 mmol) in dioxane (6 mL) is degassed. The mixture is then heated at 100° C. for 6 hours. The solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL) is added. The layers are separated and the aqueous layer is extracted with EtOAc (15 mL). The combined extracts are washed with brine (20 mL), dried (Na2SO4), and evaporated. Preparative TLC purification of the residue provides the title product. 1H NMR (CDCl3) 8.95 (s, 1H), 8.69 (s, 2H), 8.24 (d, 1H), 7.79 (d, 1H), 7.51 (t, 1H), 7.40-7.43 (m, 1H), 7.32 (s, 1H), 7.21-7.25 (m, 1H), 7.19 (s, 1H), 5.91 (s, 2H), 2.65-2.69 (m, 2H), 1.41-1.47 (m, 2H), 0.81 (t, 3H).

Provenance & Evidence