Tetrahydrofuran → ethyl 4-phenyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (50.0 mg, 0.222 mmol), phenyl boronic acid (32.4 mg, 0.266 mmol) and potassium carbonate (0.332 mL, 0.665 mmol) were added to tetrahydrofuran (1.5 mL) in a microwave vial. The solution was purged with nitrogen for 5 minutes and PdCl2(dppf)-CH2Cl2 (18 mg, 0.022 mmol) was then added. The reaction was sealed and heated at 125° C. by microwave irradiation for 30 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of desired product was carried out by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Pure fractions were pooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate and EtOAc were added to the residue. The organic layer was separated and the aqueous layer was then extracted with EtOAc (×3). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the product as a solid. LRMS (ESI) calc'd for C15H14ClN3O2 [M+H]+: 268, found 268. 1H NMR (600 MHz, DMSO-D6) δ 13.01 (s, 1H), 8.91 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.49 (m, 3H), 3.82 (q, 2H, J=7.04 Hz), 0.78 (t, 3H, J=7.04 Hz).

Provenance & Evidence