Hydrazine hydrate (1:1) → HCID 66990585, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{2-amino-6-[(cyclohexylmethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (300 mg, 0.92 mmol) in EtOH (2 mL) was added hydrazine monohydrate (3.0 mL, 61.2 mmol), and the resulting suspension was stirred at 120° C. for 1 hour under microwave conditions. The clear reaction mixture was concentrated, and the resulting residue was purified by RPHPLC (CH3CN/H2O w/0.1% THF) to afford the title compound (160 mg, 48%) as a light yellow solid. LC-MS (ES) m/z=338 [M+H]+. 1HNMR (400 MHz, DMSO-d6): δ 0.92 (m, 2H), 1.19 (m, 3H), 1.51 (m, 1H), 1.68 (m, 5H), 3.14 (s, 2H), 5.37 (s, 2H), 5.95 (s, 2H), 6.29 (s, 1H), 6.85 (bs, 1H), 7.40 (bs, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.83 (s, 1H), 11.5 (s, 1H).

Provenance & Evidence