HCID 86598743, compound → HCID 86053660, compound

Temperature

0 °C

To a vigorously stirred solution of Cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanol (0.84 g, 3.8 mmol) in anhydrous acetone (12 mL) was added portionwise chromium (VI) oxide (1.2 g, 12 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes. The excess of the oxidizing agent was destroyed by the addition of isopropanol (2 mL). After stirring for 15 minutes, the reaction mixture was poured into saturated NaHCO3 solution and filtered through Celite. The filtrate was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (hexanes:EtOAc, 6:1) to give Cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanone (0.80 g, 96%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.83 (s, 1H), 2.26 (m, 1H), 1.46 (m, 2H), 1.26 (m, 2H).

1. customThe excess of the oxidizing agent was destroyed by the addition of isopropanol (2 mL)
2. stirringAfter stirring for 15 minutes
3. additionthe reaction mixture was poured into saturated NaHCO3 solution
4. filtrationfiltered through Celite
5. extractionThe filtrate was extracted with EtOAc
6. washThe combined organic layers were washed with brine
7. customdried
8. concentrationconcentrated
9. customThe residue was purified by column chromatography (hexanes:EtOAc, 6:1)

ORD record

ord-31f471c3ebf3434eb559b9bfc9bbc7c8

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680114B2