Sodium Carbonate → 3-(4-Aminophenyl)-5-bromo-2-pyrazinamine

Participants

Reaction Conditions

Reaction Steps

A suspension of 3,5-dibromopyrazin-2-amine (CAS No. 957230-70-5) (15 g), Pd(PPh3)4 (3.2 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (12 g), and Na2CO3 (12 g) in a 3 to 1 mixture of dioxane/water (600 mL) was degassed with a stream of nitrogen for 10 minutes. The reaction was heated at 90° C. overnight, at which time LC/MS indicated the reaction was complete. The mixture was concentrated, diluted with water (200 mL) and extracted with EtOAc (3×300 mL). The organic layers were combined, dried over Na2SO4, and evaporated under reduced pressure. The crude solid was triturated with a 1 to 1 mixture of DCM/MTBE (100 mL) to give the title compound (11 g) having the following physical data as a yellow solid.

Provenance & Evidence