2,4,5-Trichloropyrimidine → 2,5-Dichloro-4-methylpyrimidine

Temperature

-78 °C

2,4,5-Trichloropyrimidine (250 mg, 1.36 mmol) and ferric acetylacetonate (24 mg, 0.07 mmol) were taken up in tetrahydrofuran (2.7 mL) and the reaction was cooled to −78° C. Methylmagnesium bromide (0.45 mL of 3 M in THF, 1.36 mmol) was added dropwise and the mixture was stirred at −78° C. for one hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by Chromatography on silica gel (0-10% diethylether in hexanes) to provide 2,5-dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45%) as a white solid. MS ESI: [M+H]+ m/z 163.0.

1. customThe mixture was quenched with aqueous ammonium chloride
2. extractionextracted with ethyl acetate
3. dry with materialThe combined organic fractions were dried over magnesium sulfate
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure
6. customThe resulting residue was purified by Chromatography on silica gel (0-10% diethylether in hexanes)

ORD record

ord-c5223ed3dd58426986979d6de3b84460

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551984B2