Ammonium Chloride → 1-(5-Pyrimidinyl)ethanone

Temperature

-78 °C

5-Bromopyrimidine (3.18 g, 20 mmol) was dissolved in 50 mL of tetrahydrofuran. While cooled to −78° C., 15 mL of 1.6 M n-butyllithium in hexane solution was added dropwise with stirring. After the solution was stirred for 30 minutes, a solution of N-methoxyl-N-methylacetamide (2.58 g, 25 mmol) in tetrahydrofuran solution (10 mL) was added slowly. The mixture was stirred at −78° C. for 1 hour and then allowed to be warmed slowly. When the temperature of the mixture was at 0° C., aqueous ammonium chloride solution was added. The solution obtained was extracted with ethyl acetate for 3 times. The pooled extracts were washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography using 5% methanol/methylene chloride as eluent to obtain 1 g of the title compound (45% yield). MS (M+1)=123.05.

1. stirringAfter the solution was stirred for 30 minutes
2. stirringThe mixture was stirred at −78° C. for 1 hour
3. temperatureto be warmed slowly
4. customwas at 0° C.
5. customThe solution obtained
6. extractionwas extracted with ethyl acetate for 3 times
7. washThe pooled extracts were washed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. custompurified by silica gel column chromatography

ORD record

ord-45d6d63bdc1c474c944af0ff1086b43e

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703771B2