Acetone → 1-(Pyrimidin-2-yl)propan-2-one

In a 100 mL flask, acetone (1.44 mL, 19.6 mmol) was added to KH (30% in oil, 2.89 g, 21.6 mmol) in THF (15 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 0.25 h then additional THF (15 mL) was added. AIBN (74 mg, 0.45 mmol) followed by 2-chloropyrimidine (500 mg, 4.36 mmol) were added cautiously and the reaction mixture kept at 0° C. for 1 h. HCl 3N was added until the pH=6. The two layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: EtOAc/pentane 20/80 to 80/20) to give the title compound (247 mg, 42%) as a yellow oil (keto/enol form 2:1).

1. additionwere added cautiously
2. waitthe reaction mixture kept at 0° C. for 1 h
3. customThe two layers were separated
4. extractionthe aqueous phase extracted with dichloromethane
5. dry with materialThe combined extracts were dried over Na2SO4
6. concentrationthen concentrated
7. customThe residue was purified on column chromatography (eluent: EtOAc/pentane 20/80 to 80/20)

ORD record

ord-fe8c1af39bf74bdc8761ace663a502b2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846711B2