1H-1,2,4-Triazole → HCID 58166479, compound

Temperature

70 °C

To a mixture of 1,2,4-triazole (0.044 g, 0.64 mmol), potassium tbutoxide (KOtBu; 0.072 g, 0.64 mmol), and 18-crown-6 (18C6; 0.008 g, 0.03 mmol) in CH3CN (3.5 mL) was added 4-amino-5-fluoro-1-(4-iodobutyl)-1H-pyrimidin-2-one (0.10 g, 0.32 mmol), and the mixture was warmed to 70° C. and stirred for 16 h. The resulting homogeneous solution was concentrated in vacuo to give the crude product as a white solid. Purification by reverse phase chromatography (13 g C18; gradient, 0 to 20% CH3CN/water) afforded 4-amino-5-fluoro-1-(4-[1,2,4]triazol-1-yl-butyl)-1H-pyrimidin-2-one (0.023 g, 28%) as a white solid: mp 197-200° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.94 (m, 2H), 7.56 (s, 1H), 7.35 (s, 1H), 4.19 (t, J=6.9 Hz, 2H), 3.61 (t, J=7.0 Hz, 2H), 1.73 (m, 2H), 1.51 (m, 2H); ESIMS m/z 253 ([M+H]+), m/z 251 ([M−H]−).

1. concentrationThe resulting homogeneous solution was concentrated in vacuo
2. customto give the crude product as a white solid
3. customPurification by reverse phase chromatography (13 g C18; gradient, 0 to 20% CH3CN/water)

ORD record

ord-12247965af6a482c96c8d6b0da405362

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916579B2