Sodium hydride → HCID 58515275, compound

Temperature

0 °C

To a solution of (R)-(−)-3-hydroxytetrahydrofuran (0.9 g, 10.2 mmol) in 1.2 mL anhydrous THF at 0° C. was added NaH (60% in mineral oil, 100 mg, 2.5 mmol). The mixture was stirred at 0° C. for 5 min and then r.t. for 2 h until there was no hydrogen bubbles generated. This mixture was added slowly to a solution of 5-bromo-2,4-dichloropyrimidine (570 mg, 2.5 mmol) and (R)-(−)-3-hydroxytetrahydrofuran (0.1 g, 1.1 mmol) in 0.8 mL THF at −10° C., and then the reaction mixture was stirred at the same temperature for 30 min. The reaction was quenched with water and extracted with EtOAc. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue was purified using ISCO chromatography (40 g silica gel, 1-20% EtOAc in hexanes in 40 min) to give the title compound (285 mg, 41%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.45 (s, 1H), 5.69-5.66 (m, 1H), 4.11-3.91 (m, 4H), 2.36-2.21 (m, 2H).

1. waitr.t. for 2 h until there was
2. stirringthe reaction mixture was stirred at the same temperature for 30 min
3. customThe reaction was quenched with water
4. extractionextracted with EtOAc
5. customThe organic layer was separated
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified
9. customISCO chromatography (40 g silica gel, 1-20% EtOAc in hexanes in 40 min)

ORD record

ord-231ee2dc6c6f4fc784cc7a809fb52103

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513242B2