3-Oxotetrahydrofuran → HCID 89923682, compound

Temperature

-78 °C

5-Bromo-2-iodopyrimidine (10 g, 35.1 mmol) was dissolved in dry toluene (100 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 14.7 mL) was added dropwise and the reaction mixture was aged for 30 minutes prior to dropwise addition of oxolan-3-one (2.97 mL, 38.6 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature for 1 h. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed successively with water and brine, then dried over magnesium sulphate. The solvent was removed under reduced pressure to afford a dark yellow oil. The crude material was purified by chromatography on silica (Biotage, 100 g cartridge), eluting with 0-100% ethyl acetate in heptanes, to afford the title compound (2.15 g, 25% at 86% purity) as a yellow oil. δH (500 MHz, DMSO-d6) 9.01 (s, 2H), 5.66 (s, 1H), 3.99-3.93 (m, 2H), 3.88-3.77 (m, 2H), 2.46 (dt, J 12.6, 8.9 Hz, 1H), 2.16 (ddd, J 12.6, 6.4, 3.5 Hz, 1H).

1. temperatureto warm to room temperature for 1 h
2. extractionextracted with ethyl acetate (3×200 mL)
3. washThe combined organic extracts were washed successively with water and brine
4. dry with materialdried over magnesium sulphate
5. customThe solvent was removed under reduced pressure
6. customto afford a dark yellow oil
7. customThe crude material was purified by chromatography on silica (Biotage, 100 g cartridge)
8. washeluting with 0-100% ethyl acetate in heptanes

ORD record

ord-7d4e0315e0ab45b2837799ef39f27430

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2