2H-Pyran-3(4H)-one, dihydro- → HCID 86706969, compound

Temperature

-78 °C

To a −78° C. solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.5 g, 5.4 mmol) in tetrahydrofuran (50 mL) was added n-butyllithium (2.5 M, 6.4 mL, 16.1 mmol) drop-wise. After the reaction mixture had been stirred at −78° C. for 2 hours, it was treated with dihydro-2H-pyran-3(4H)-one (1.61 g, 16.1 mmol), warmed to room temperature, and stirred for 18 hours. The reaction was quenched with water (50 mL), and the aqueous layer was extracted with ethyl acetate (3×30 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentrated. Silica gel chromatography (Gradient: 0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow oil. Yield: 200 mg, 0.79 mmol, 15%. LCMS m/z 254.0 [M+H+].

1. temperaturewarmed to room temperature
2. stirringstirred for 18 hours
3. customThe reaction was quenched with water (50 mL)
4. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
5. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-31b3af427b204210864ea8d0e8be26f9

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156845B2