Ethyl Acetate → (5-Amino-2-phenyl-furo[2,3-d]pyrimidin-6-yl)-(2,4-dichloro-phenyl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-hydroxy-2-phenyl-pyrimidine-5-carbonitrile (12) (50 mg, 0.25 mmol, from step 1) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (85 mg, 0.38mmol, 1.5 equiv) in anhydrous N,N-dimethylformamide (1.0 mL) was added NaOH (30.4 mg, 0.76 mmol, 3.0 equiv). The dark brown reaction mixture was stirred at 110° C. for 12 h. The reaction was then poured into ethyl acetate (10 mL) and water (10 mL). Extracted with ethyl acetate (3×10 mL). The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. The crude product was purified by pre-HPLC to provide 9.1 mg (9.3%) of the desired compound as yellow solid. 1H-NMR (CD3CN) δ 9.36 (s, 1H), 8.50 (d, 2H), 7.66 (d, 1H), 7.55 (m, 5H); MS LC-MS (MH+=384/386).

Provenance & Evidence