Ethyl Acetate → 6-{2-Amino-6-[(2R)-2-ethyl-1-pyrrolidinyl]-4-pyrimidinyl}-1H-indazol-3-amine

Participants

Reaction Conditions

Reaction Steps

To 4-{2-amino-6-[(2R)-2-ethyl-1-pyrrolidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (50 mg, 0.161 mmol) in ethanol (4 mL) was added hydrazine monohydrate (1 mL, 20.40 mmol), and the reaction mixture was stirred overnight at 100° C. into a sealed tube. The reaction was poured onto water and EtOAc, and the organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting solid was dissolved in ethanol (˜2 mL), and treated with hexanes until the solution became cloudy. The mixture was roto-evaporated (˜½ original volume) until a heavy precipitate was observed. The solution was decanted and the solid was dried under vacuum at 40° C. to afford the title compound (30 mg, 58%) as a pale yellow solid. LC-MS (ES) m/z=324 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.89 (t, J=7.3 Hz, 3H), 1.37 (m, 1H), 1.7-2.0 (m, 5H), 3.40 (m, 1H), 3.50 (m, 1H), 4.00 (m, 1H), 5.38 (bs, 2H), 5.97 (bs, 2H), 6.23 (s, 1H), 7.51 (dd, J=8.6, 1.0 Hz, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.89 (s, 1H), 11.49 (s, 1H).

Provenance & Evidence