Sodium Hydroxide → 4-(4-(1-Ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)phenol

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Reaction Steps

A mixture of (E)-3-(dimethylamino)-1-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one (5 mmol) in 3 mL EtOH/MeOH (1:2, v/v) was treated with 1-(4-hydroxyphenyl)guanidine hydrochloride (5 mmol) and NaOH (10 mmol). The reaction mixture was microwaved at 150° C. for 25 minutes. The residue was purified by chromatography using EtOAc to elute the titled compound. Recrystallisation from EtOAc yielded white solid. 1H-NMR (DMSO-d6) δ: 1.45 (t, 3H, J=7.2 Hz, CH3), 4.37 (q, 2H, J=7.6 Hz, CH2), 6.74 (d, 2H, J=8.8 Hz, Ph-H), 7.15 (d, 1H, J=5.2 Hz, Pyrimidin-H), 7.20 (q, 1H, J=4.8 Hz, Ar—H), 7.51 (d, 2H, J=8.8 Hz, Ph-H), 8.29 (d, 1H, J=5.2 Hz, Pyrimidin-H), 8.35 (m, 1H, Ar—H), 8.54 (s, 1H, Ar—H), 8.88 (d, 1H, J=6.8 Hz, OH), 9.04 (s, 1H, Ar—H), 9.10 (s, 1H, NH). MS (ESI+) m/z 322.1469 (M+H)+.

Provenance & Evidence