Tetrahydrofuran → 1-(5-Bromopyrimidin-2-yl)ethan-1-one

Temperature

-78 °C

To a solution of 5-bromopyrimidine-2-carbonitrile (221 mg, 1.2 mmol) in THF (10 ml) was added methylmagnesium bromide (3.0 ml, 4.20 mmol, 1.4 molar, THF) at −78° C. under nitrogen. The solution was stirred at −78° C. for 3.5 hours, and then quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 1-(5-bromopyrimidin-2-yl)ethanone (1.55 mg, 61% yield). 1H NMR (CDCl3 500 MHz): δ 9.00 (s, 2H), 2.80 (s, 3H).

1. customquenched with satd aq NH4Cl
2. extractionextracted with EtOAc
3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
4. concentrationconcentrated
5. customThe reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)

ORD record

ord-71a37e665ded4f3a9f8e1cbfe2daea43

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108938B2