Sodium Carbonate → 5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 2) (1 eq, 1.94 mmol, 500 mg) and 3-ethoxycarbonylpyridine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA) (1.5. eq, 2.91 mmol, 820 mg) in DME/EtOH (1:1, 6 ml), aqueous Na2CO3 solution (2 M, 3 eq, 5.80 mmol, 2.9 ml) and Pd(PPh3)4 (0.05 eq, 0.097 mmol, 116 mg) are added. The resulting mixture is heated using microwave radiation at 120° C. for 20 min. The solvents are evaporated and the remaining residue is suspended in MeOH (30 ml). The mixture is cooled to 0° C., then aqueous NaOH solution (1 M, 1.9 eq, 3.60 mmol, 3.6 ml) is added. After stirring for 10 min at this temperature, the mixture is allowed to warm up to r.t. and stirred for another 1 h. After cooling down to 0° C., glacial acetic acid (5 ml) and water (100 ml) are added. The resulting precipitate is filtered and washed with water giving the title compound; [M+H]+=332.

Provenance & Evidence