Potassium Carbonate → HCID 58166432, compound

To a solution of (bromomethyl)cyclopropane (1.0 g, 7.4 mmol) in DMF (20 mL) was added molecular sieves (—2 g), and the resulting mixture was stirred at room temperature. After 1 h, 4-amino-5-fluoropyrimidin-2-ol (1.9 g, 14.8 mmol) and K2CO3 (5.1 g, 37 mmol) were added, and the reaction mixture was heated at 90° C. for 12 h. After cooling to room temperature, the crude reaction mixture was filtered through a Büchner funnel, and the solid residue was washed with EtOAc. The collected filtrate was concentrated in vacuo to give a residue which was purified by normal phase chromatography (isocratic, 5% MeOH/EtOAc). Following recrystallization from methyl tert-butylether, 4-amino-1-(cyclopropylmethyl)-5-fluoropyrimidin-2(1H)-one (1.12 g, 83%) was isolated as a white solid: mp 224-226° C.; 1H NMR (400 MHz, methanol-d4) δ 7.86 (d, J=6.2 Hz, 1H), 3.61 (d, J=7.2 Hz, 2H), 1.24 (ddd, J=12.8, 7.6, 4.8 Hz, 1H), 0.65-0.50 (m, 2H), 0.39 (q, J=4.8 Hz, 2H); ESIMS m/z 184 ([M+H]+).

1. temperaturethe reaction mixture was heated at 90° C. for 12 h
2. temperatureAfter cooling to room temperature
3. customthe crude reaction mixture
4. filtrationwas filtered through a Büchner funnel
5. washthe solid residue was washed with EtOAc
6. concentrationThe collected filtrate was concentrated in vacuo
7. customto give a residue which
8. customwas purified by normal phase chromatography (isocratic, 5% MeOH/EtOAc)
9. customrecrystallization from methyl tert-butylether

ORD record

ord-1bd6be29042549d28d75450ccbaee7cc

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916579B2