Methyl 5-amino-6-(phenylamino)-2-(3-pyridyl)pyrimidine-4-carboxylate. To a solution of methyl 5-amino-2-chloro-6-(phenylamino)pyrimidine-4-carboxylate (0.189 g, 0.68 mmol) in anhydrous DMF (3.5 mL) was added 3-(tributylstannyl)pyridine (1.252 g, 3.4 mmol), and dichlorobis(triphenylphosphine) palladium(II) (0.239 g, 0.34 mmol). The solution was purged with nitrogen then heated in an Emrys Optimizer microwave reactor for 30 minutes at 120° C. The volatiles were evaporated and the resulting residue was purified using chromatography on a normal phase silica gel column (1-10% methanol in dichloromethane). Fractions containing product were combined and the solvent evaporated. The material was re-purified using reverse-phase preparatory HPLC (30-80% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 minutes). Fractions containing the desired material were combined and concentrated under reduced pressure before being passed through a Strata-XC ion exchange column with water, methanol, and 5% ammonium hydroxide in methanol. The resulting solid was dried under high vacuum at 60° C. to afford the title compound (0.125 g, 0.389 mmol, 57% yield). MS (ESI) m/z 322.4 [M+1]+.
