Water → HCID 58166428, compound

Participants

Reaction Steps

Phosphoryl trichloride (3.3 g, 21 mmol) was added to a solution of 1,2,4-triazole (6.7 g, 97 mmol) in CH3CN (53 mL) under nitrogen at room temperature. The mixture was cooled to 0° C., whereupon triethylamine (Et3N, 9.5 g, 92 mmol) was added dropwise followed by the addition of a solution of 5-fluoro-1-isobutylpyrimidine-2,4(1H,3H)-dione (2.0 g, 11 mmol) in CH3CN (30 mL). After stiffing for 1 h at room temperature, Et3N (3.6 g, 36 mmol) and then water (5 mL, 280 mmol) were added, and the reaction mixture was stirred for an additional 10 min. The crude reaction mixture was then concentrated in vacuo. Recrystallization from EtOAc/petroleum ether provided 5-fluoro-1-isobutyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (1.9 g, 74%) as an off white crystalline solid: mp 150-153° C.; 1H NMR (400 MHz, CDCl3) δ 9.26 (s, 1H), 8.23 (s, 1H), 7.84 (d, J=5.7 Hz, 1H), 3.79 (d, J=7.4 Hz, 2H), 2.28 (dt, J=13.7, 6.9 Hz, 1H), 1.02 (d, J=6.7 Hz, 6H); ESIMS m/z 238 ([M+H]+).

Provenance & Evidence