Nitrogen → 4-(2-Amino-6-{[(2-chlorophenyl)methyl]amino}-4-pyrimidinyl)-2-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-N4-[(2-chlorophenyl)methyl]-2,4-pyrimidinediamine (1.2 g, 4.46 mmol) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.32 g, 5.35 mmol) in 1,4-dioxane (14.6 mL) and a solution of NaHCO3 (3.12 mmol) in water (20 mL) was protected with N2. Pd(Ph3P)4 (100 mg, 0.087 mmol) was added, and the reaction mixture was heated at 100° C. for 16 hours. The mixture was decanted to remove the solids, and the resulting solution was concentrated to dryness. The crude material was purified by SiO2 chromatography (1:2 THF:petroleum ether) to afford the title compound (800 mg) as a yellow solid. LC-MS (ES) m/z=354 [M+H]+.

Provenance & Evidence