2,4-Dichloro-5-fluoropyrimidine → 2-Chloro-5-fluoro-4-methoxypyrimidine

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-5-fluoropyrimidine (515 mg, 3.08 mmol) was weighed into a 150 mL RBF, and was suspended in THF (5.0 mL). The stirring suspension was cooled to −10° C. NaOMe (250 mg, 4.63 mmol) was added in one portion at −10° C. An additional 0.5 eq of NaOMe were added and the suspension was stirred at RT for 21 h. The suspension was diluted with MeOH, and the solvents were removed in vacuo. The crude material was purified by flash chromatography (eluting with 100% DCM) to give 2-chloro-5-fluoro-4-methoxypyrimidine (37 mg, 0.228 mmol, 7.38%) as an amorphous white solid. MS (ESI, pos. ion) m/z: 162.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (d, J=2.7 Hz, 1H), 4.04 (s, 3H).

Provenance & Evidence