3-Fluoro-4-methoxyphenylboronic acid → 2-benzyl-5-(3-fluoro-4-methoxyphenyl)-3-methyl-3H-pyrimidin-4-one

Participants

Reaction Steps

2-Benzyl-5-bromo-3-methyl-3H-pyrimidin-4-one (Step 3, 11.1 g, 39.9 mmol), 4-methoxy-3-fluorophenylboronic acid (10.12 g, 59 mmol) and Pd(PPh3)4 (2.3 g, 1.9 mmol) in 2 M Na2CO3 (100 mL) and dioxane (150 mL) were heated to 90° C. for 1 h. The reaction was cooled to RT, and diluted with H2O and CH2Cl2. The organics were separated and washed with brine, dried (Na2SO4) and filtered through a plug of silica. The filtrate was concentrated under reduced pressure. Et2O/hexane (1:1) were added and the reaction was concentrated under vacuum to a brown solid. The solid was triturated with 20% Et2O/hexane to afford the title compound as a yellow solid. MS (ESI pos. ion) m/z: 325.2. Calc'd for C19H17FN2O2: 324.13.

Provenance & Evidence