Tetrahydro-4H-pyran-4-one → HCID 89810983, compound

Temperature

-78 °C

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 2.95 mL) was added dropwise, and the reaction mixture was aged for 15 minutes prior to dropwise addition of tetrahydro-4H-pyran-4-one (0.77 g, 7.72 mmol). The reaction was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over magnesium sulphate and filtered, then the solvent was removed under reduced pressure. The resulting crude orange oil (1.91 g) was absorbed onto a 50 g KP-Sil column, and eluted with 10-100% ethyl acetate in heptanes on a Biotage Isolera 4, to afford the title compound (762 mg, 42%) as a yellow oil. δH (500 MHz, CDCl3) 8.79 (s, 2H), 4.24 (s, 1H), 3.99-3.89 (m, 4H), 2.37 (td, J 12.3, 11.6, 6.3 Hz, 2H), 1.54 (dd, J 13.6, 2.0 Hz, 2H).

1. temperatureto warm to room temperature
2. extractionextracted with ethyl acetate (2×50 mL)
3. dry with materialThe combined organic extracts were dried over magnesium sulphate
4. filtrationfiltered
5. customthe solvent was removed under reduced pressure
6. customThe resulting crude orange oil (1.91 g) was absorbed onto a 50 g KP-Sil column
7. washeluted with 10-100% ethyl acetate in heptanes on a Biotage Isolera 4

ORD record

ord-a98172c345da4a5c85ddb7d519d755ed

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2