Benzyl chloromethyl ether → HCID 58166413, compound

Temperature

65 °C

A 25 mL Schlenk-type flask was charged with 4-amino-5-fluoropyrimidin-2-ol (500 mg, 3.87 mmol), CH3CN (10 mL), and BSA (1.42 mL, 5.81 mmol). The resulting white suspension was then heated at 65° C. After 90 min, the clear, colorless solution was cooled to room temperature and benzyl chloromethyl ether (1.07 mL, 7.72 mmol) was added, giving a cloudy white suspension. After stirring for 2 h at room temperature, the reaction mixture was concentrated in vacuo to give a white residue which was purified by reverse phase column chromatography yielding 4-amino-1-(benzyloxymethyl)-5-fluoropyrimidin-2(1H)-one (14; 433 mg, 45%) as a white solid: mp 213-217° C.; 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=6.5 Hz, 1H), 7.81 (br s, 1H), 7.56 (br s, 1H), 7.24-7.36 (m, 5H), 5.11 (s, 2H), 4.54 (s, 2H); IR 3302 (s), 3082 (s), 2939 (w), 2869 (w), 1688 (s), 1619 (s), 1522 (s), 1468 (m), 1333 (m), 1131 (w), 1054 (m) cm−1; ESIMS m/z 250 ([M+H]+).

1. temperaturethe clear, colorless solution was cooled to room temperature
2. customgiving a cloudy white suspension
3. concentrationthe reaction mixture was concentrated in vacuo
4. customto give a white residue which
5. customwas purified by reverse phase column chromatography

ORD record

ord-a3e2f4f4cf804240860952a5781ba497

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916579B2