Sodium hydride → HCID 86761730, compound

Participants

Reaction Steps

To a solution of 3-hydroxyoxetane (76 mg, 1.02 mmol) in anhydrous THF (8 mL) at r.t. was added NaH (60% in mineral oil, 39 mg, 0.97 mmol). The mixture was stirred at r.t. for 5 min until there was no hydrogen bubbles generated. 5-bromo-2,4-dichloro-6-(methoxymethyl)pyrimidine (1) (250 mg, 0.93 mmol) was added and the resulting reaction mixture was stirred at r.t. overnight. The reaction was quenched with aqueous NH4Cl and extracted with EtOAc. The organic layer was separated, washed with aqueous NaHCO3, and dried (Na2SO4) and concentrated in vacuo. The residue was purified using ISCO chromatography (24 g silica gel, 0-20% EtOAc in hexanes in 40 min) to give the title compound (207 mg, 73%) as a white solid. 1H NMR (DMSO, 500 MHz) δ 5.57-5.52 (m, 1H), 4.91-4.86 (m, 2H), 4.68 (s, 2H), 4.61-4.57 (m, 2H), 3.98 (s, 3H).

Provenance & Evidence