Sodium hydride → HCID 58515275, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence