Hydrazine hydrate (1:1) → HCID 46215128, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2S,5R)-4-[6-(4-cyano-3-fluorophenyl)-2-(methylamino)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide (340 mg, 0.61 mmol) and hydrazine monohydrate (0.39 mL, 12.54 mmol) in 1,4-dioxane (5 mL) was stirred at 100° C. in a sealed tube for 18 hours. The reaction mixture was cooled and concentrated in vacuo, and the residue was purified by flash chromatography (60 g SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (243 mg) as a pale yellow solid. LC-MS (ES) m/z=459 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.24 (d, J=6.6 Hz, 3H), 2.86 (d, J=4.0 Hz, 3H), 2.97-3.15 (m, 1H), 3.83 (d, J=11.1 Hz, 1H), 3.94 (d, J=11.1 Hz, 1H), 4.16 (dd, J=11.2, 2.9 Hz, 1H), 4.33-4.88 (bs, 2H), 5.39 (s, 2H), 6.56-6.73 (m, 2H), 7.10 (t, J=7.3 Hz, 1H), 7.34 (t, J=7.9 Hz, 2H), 7.63 (d, J=8.3 Hz, 1H), 7.73 (d, J=8.3 Hz, 3H), 8.01 (s, 1H), 9.88 (s, 1H), 11.51 (s, 1H).

Provenance & Evidence