Nitrogen → 5-(3-Fluoro-4-methoxyphenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

In a 500 mL round bottom flask under N2, 3-fluoro-4-methoxyphenylboronic acid (5.0 g, 29.4 mmol) and 5-iodopyrimidin-2-amine (5.5 g, 24.9 mmol) were mixed. Toluene (100 mL), EtOH (40 mL) and H2O (20 mL) were added, followed by the addition of Na2CO3 (3.0 g, 24.2 mmol). A stream of N2 was bubbled through the mixture for 5 min before the catalyst Pd(PPh)4 (0.30 g, 0.26 mmol) was added. The mixture was heated at 80° C. under N2 for 20 h whereby it was cooled to RT. A solution of NaOH (5 N, 10 mL) was added to the mixture and stirring was continued for 10 min. The mixture was filtered and the solid was washed with H2O (3×10 mL), followed by a mixture of hexanes—EtOAc (1:1, 30 mL). The solid was dried in the air to give the title compound. MS (ESI pos. ion) m/z: 220. Calc'd for C11H10FN3O: 219.08.

Provenance & Evidence