Hydrazine hydrate (1:1) → HCID 58504576, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude N-({(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-2-morpholinyl}methyl)methanesulfonamide (0.25 mmol theoretical) and hydrazine monohydrate (0.24 mL, 4.95 mmol) in 1,4-dioxane (3 mL) was stirred at 100° C. in a sealed tube for 17 hours. The mixture was concentrated in vacuo and the residue was purified on a Gilson reverse phase HPLC (CH3CN/water with 0.1% TFA). The product fractions were concentrated in vacuo, taken up in EtOAc (25 mL), washed with saturated aqueous NaHCO3 (2×15 mL) and brine (15 mL), then dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound (29 mg) as a pale yellow solid. LC-MS (ES) m/z=433 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.18 (d, J=6.6 Hz, 3H), 2.72-2.88 (m, 1H), 2.96 (s, 3H), 3.09-3.22 (m, 2H), 3.45-3.55 (m, 1H), 3.67 (dd, J=11.4, 2.5 Hz, 1H), 3.79 (d, J=11.1 Hz, 1H), 4.04-4.75 (bs, 2H), 5.39 (s, 2H), 6.14 (s, 2H), 6.56 (s, 1H), 7.23 (t, J=6.1 Hz, 1H), 7.57 (dd, J=8.6, 1.0 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.94 (s, 1H), 11.53 (s, 1H).

Provenance & Evidence