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-4eb061f5f25646bbb54edbec510ccf0d

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2