Chloromethyl ethyl ether → HCID 58166474, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL screw-top vial was charged with 5-fluoro-4-(2-fluorobenzylamino)pyrimidin-2-ol (49.7 mg, 0.210 mmol), CH3CN (1 mL), and BSA (0.054 mL, 0.0221 mmol), and the mixture was agitated on an rotary shaker at 65° C. for 30 min. After cooling to room temperature, (chloromethoxy)ethane (0.022 mL, 0.237 mmol) was added, and the resulting mixture was agitated on a rotary shaker at room temperature for 16 h. The crude reaction mixture was concentrated in vacuo and was purified by normal phase chromatography (gradient, 0 to 25% MeOH/CH2Cl2) to afford 1-(ethoxymethyl)-5-fluoro-4-(2-fluorobenzylamino)-pyrimidin-2(1H)-one (55.0 mg, 89%) as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 8.60 (t, J=5.8 Hz, 1H), 8.05-7.95 (m, 1H), 7.40-7.26 (m, 2H), 7.26-7.10 (m, 2H), 5.01 (s, 2H), 4.59 (d, J=5.9 Hz, 2H), 3.49 (q, J=7.0 Hz, 2H), 1.09 (dd, J=9.0, 5.0 Hz, 3H); ESIMS m/z 296 ([M+H]+), m/z 294 ([M−H]−).

Provenance & Evidence