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

Temperature

-10 °C

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).

1. customthe solvents were removed in vacuo
2. customThe crude material was purified by flash chromatography (eluting with 100% DCM)

ORD record

ord-e1777eeecfc842818ce2e0f9af7117dc

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321756B2