1,4-Diiodobutane → HCID 58166461, compound

Temperature

70 °C

To a suspension of 4-amino-5-fluoropyrimidin-2-ol (0.50 g, 3.87 mmol) in acetonitrile (CH3CN; 20 mL) was added BSA (1.58 g, 7.75 mmol), and the mixture was heated to 70° C. for 1 h resulting in a clear solution. After cooling to room temperature, 1,4-diiodobutane (1.2 g, 3.87 mmol) was added, and the mixture was stirred for 16 h at room temperature and then at 70° C. for 3 h. The solvent was evaporated and the residue was purified by normal phase chromatography (24 g SiO2; gradient, 0 to 15% MeOH/CH2Cl2) to give an orange oil. The oil was dissolved in EtOAc and the solution was slowly cooled. The resulting solid was collected by filtration, washed with additional EtOAc, and dried to give 4-amino-5-fluoro-1-(4-iodobutyl)-1H-pyrimidin-2-one (0.52 g, 43%) as a tan solid: mp 181-184° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 2H), 8.25 (d, J=6.7 Hz, 1H), 3.70 (t, J=6.7 Hz, 2H), 3.29 (t, J=6.7 Hz, 2H), 1.73 (m, 4H); ESIMS m/z 312 ([M+H]+).

1. additionwas added BSA (1.58 g, 7.75 mmol)
2. customresulting in a clear solution
3. temperatureAfter cooling to room temperature
4. waitat 70° C. for 3 h
5. customThe solvent was evaporated
6. customthe residue was purified by normal phase chromatography (24 g SiO2; gradient, 0 to 15% MeOH/CH2Cl2)
7. customto give an orange oil
8. temperaturethe solution was slowly cooled
9. filtrationThe resulting solid was collected by filtration
10. washwashed with additional EtOAc
11. customdried

ORD record

ord-eb0cfba9991e446a9c935a0150974a70

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916579B2