Hydrazine hydrate (1:1) → HCID 58504735, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[6-{(2R,5R)-2-[(dimethylamino)methyl]-5-methyl-4-morpholinyl}-2-(methylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (58 mg, 0.15 mmol) and hydrazine monohydrate (0.10 mL, 3.21 mmol) in 1,4-dioxane (2 mL) was stirred at 100° C. in a sealed tube for 15 hours. The reaction mixture was then cooled and concentrated in vacuo, and the residue was purified by flash chromatography (24 g SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (44 mg) as an off-white solid. LC-MS (ES) m/z=397 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.17 (d, J=6.6 Hz, 3H), 2.22 (s, 6H), 2.35-2.45 (m, 2H), 2.66-2.80 (m, 1H), 2.84 (d, J=4.3 Hz, 3H), 3.49-3.60 (m, 1H), 3.66 (d, J=11.4 Hz, 1H), 3.75 (d, J=11.1 Hz, 1H), 4.02-4.79 (bs, 2H), 5.38 (s, 2H), 6.48-6.65 (m, 2H), 7.60 (d, J=8.6 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H), 7.98 (s, 1H), 11.50 (s, 1H).

Provenance & Evidence