Hydrazine hydrate (1:1) → HCID 178490034, compound

Participants

Reaction Steps

2-[2-chloro-6-(2(S)-hydroxypropylamino)pyrimidin-4-yl]-1-(3-methoxy-5-methylphenyl)ethanone (2.16 g, 6.17 mmol) was heated at 90° C. for 20 hours together with N,N-dimethylformamide dimethylacetal (8.23 mL, 61.7 mmol). Excess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation, and the reaction mixture was dissolved in anhydrous ethanol (50 mL). To this solution was dropwise added hydrazine hydrate (617 μL, 12.35 mmol), and stirred at room temperature for 12 hours. After completion of the cyclization, the solvent was removed by vacuum distillation. The concentrate was treated in water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under vacuum. Recrystallization in dichloromethane gave the title compound (1.01 g, 44%).

Provenance & Evidence