Hydrazine hydrate (1:1) → 6-(3-Amino-1H-indazol-6-yl)-N4-[1-(phenylmethyl)cyclopropyl]-2,4-pyrimidinediamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-amino-6-{[1-(phenylmethyl)cyclopropyl]amino}-4-pyrimidinyl)-2-fluorobenzonitrile (124 mg, 0.34 mmol) and hydrazine hydrate (99%, 2 mL) in ethanol (10 mL) was stirred and heated at 120° C. for 1 hour in a Biotage Initiator microwave synthesizer. The mixture was cooled to room temperature, filtered and concentrated in vacuo. The resulting solids were purified by reverse phase chromatography with CH3CN in water (0.08% ammonium hydrogen carbonate) (gradient: 35% to 45% in 6 min: flowrate: 30 mL/min), to afford the title compound (30 mg) as a white solid. LC-MS (ES) m/z=372 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.78 (d, 4H), 2.93 (s, 2H), 5.37 (s, 2H), 5.97 (s, 2H), 6.32 (s, 1H), 6.90 (s, 1H), 7.18 (d, 3H), 7.27 (t, 2H), 7.40 (s, 1H), 7.69 (d, 1H), 7.81 (s, 1H), 11.50 (s, 1H).

Provenance & Evidence