Bromobenzene → 5-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(3-fluoro-4-methoxyphenyl)pyrimidin-2-amine (Step 1, 0.44 g, 2.0 mmol) and bromobenzene (0.60 g, 4.0 mmol) in N,N′-dimethylacetamide (1.0 mL) and toluene (1.0 mL) was placed in a microwave tube and was treated with Pd(OAc)2 (0.024 g, 0.1 mmol), 2-biscyclohexyl 1,1-biphenyl phosphine (Strem Chemical, 0.070 g, 0.20 mmol), and KOtBu (0.44 g, 4.0 mmol). The mixture was degassed with N2 (2×) and was subject to microwave heating at 200° C. for a total of 20 min. After the mixture was cooled to RT, it was filtered through a pad of Celite®. The solid was washed with EtOAc (3×10 mL), and the combined organic phase was washed with H2O, NH4Cl (sat.), dried with Na2SO4, and concentrated to an oil. Purification on silica using hexanes-EtOAc (3:1) resulted the desired compound as a yellow solid. MS (ESI pos. ion) m/z: 296. Calc'd for C17H14FN3O: 295.11.

Provenance & Evidence