p-Fluoronitrobenzene → 1-(4-aminophenyl)pyrimidin-2(1H)-one

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Reaction Steps

2-Hydroxypyrimidine hydrogenchloride (2.1, 1.50 g, 11.3 mmol) was stirred in 20 mL dry NMP at RT. To it was added sodium hydride (60% in mineral oil, 0.95 g, 23.5 mmol) in small portions carefully. The mixture was stirred for 30 min before 4-fluoro-1-nitrobenzene (1.0 mL, 9.4 mmol) was added. The mixture was sent to 80° C. bath and stirred overnight. It was concentrated in vacuo and taken into acetonitrile. After vigorously stirring, the insoluble solid was collected, which was a mixture of leftover 2-hydroxypyrimidine and 1-(4-nitrophenyl)pyrimidin-2(1H)-one 2.2. MS found for C10H7N3O3 (M+H)+ 218.0. This solid (1.27 g, 5.8 mmol) was dissolved in 100 mL ethanol and 30 mL water. To it was added ammonium chloride (3.1 g, 58 mmol) and indium powder (2.6 g, 23 mmol). The mixture was refluxed for 6 hrs. It was concentrated in vacuo, filtered through celite. The solid cake was rinsed with water. The filtrate was concentrated and subjected to reverse phase prep HPLC to isolate 1-(4-aminophenyl)pyrimidin-2(1H)-one 2.3. MS found for C10H9N3O (M+H)+ 188.1.

Provenance & Evidence