Sodium Carbonate → 4-Pyridin-3-yl-2-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

4-Chloro-2-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 1) (1 eq, 1.17 mmol, 285 mg) and pyridine-3-boronic acid (ABCR GmbH & Co. KG, Karlsruhe, Germany) (2 eq, 2.35 mmol, 294 mg) are dissolved in MeCN (8 ml). Then an aqueous Na2CO3 solution (2 M, 4 eq, 4.7 mmol, 2.3 ml) and PdCl2(PPh3)2 (0.1 eq, 0.117 mmol, 84 mg) are added and the resulting mixture is heated using microwave radiation at 150° C. for 20 min. Alternatively Pd(PPh3)4 and DME/EtOH (1:1) can be used instead of PdCl2(PPh3)2 and MeCN. The solvents are removed in vacuo, then aqueous NaOH solution (1 M) is added, and the solution is extracted with DCM. The organic layer is dried with MgSO4, filtered, and concentrated. The crude product is recrystallized from EtOAc affording the title compound; [M+H]+=274; 1H-NMR (400 MHz, DMSO): δ 12.52 (s, 1H), 9.46 (dd, 1H), 8.76 (m, 2H), 8.66 (td, 1H), 8.57 (td, 1H), 7.97 (dt, 1H), 7.80 (d, 1H), 7.65 (ddd, 1H), 7.48 (ddd, 1H), 7.01 (d, 1H).

Provenance & Evidence