Ethyl Acetate → 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-(3-methoxypropyl)pyrimidine-2,4-diamine

Participants

Reaction Steps

To a solution of 2-(5-(2-((3-fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (J6, 90 mg) in tetrahydrofuran (1 mL) and ethanol (0.5 mL), hydrazine monohydrate (100 μL) was added at room temperature, and the mixture was stirred for 1 hour under reflux by heating. The reaction mixture was cooled to room temperature, and then ethyl acetate was added to the reaction mixture. The insoluble matter was removed by filtration, and then 1.0 mol/L aqueous hydrochloric acid was added to the reaction mixture until the mixture became acidic. The aqueous layer was separated, 3.0 mol/L aqueous sodium hydroxide was added until the mixture became basic, and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-(3-methoxypropyl)pyrimidine-2,4-diamine (J7, 55 mg) as pale yellow solid.

Provenance & Evidence