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 Combiflash (0-10% diethylether in hexanes) to provide 2,5-dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45%) as a white solid. MS APCI: [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 Combiflash (0-10% diethylether in hexanes)

ORD record

ord-2464c4ca79d847dda63eb4273acb16c4

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735417B2