Acetyl chloride → Methyl 5-bromopyrimidine-2-carboxylate

To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated to give methyl 5-bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67% yield) as a white solid. LC/MS (ESI+) m/z=216.9 (M+H). Calculated for C6H5BrN2O2 216.0.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 15 min
3. concentrationconcentrated under reduced pressure
4. additionThe reaction mixture was diluted with saturated NaHCO3 (30 mL) and EtOAc
5. customtransferred to a separatory funnel
6. extractionThe aqueous phase was extracted with EtOAc (4×)
7. washthe combined organic extracts were washed with brine (1×)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-ba664f7735fd4a87bdaa5bdd5d799fe6

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2