Sodium hydride → HCID 22288415, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-phenylimidazole (1-2, 484 mg, 3.36 mmol) in dry THF (15 mL) was added NaH (130 mg, 60% dispersion in mineral oil, 3.36 mmol) at room temperature. After gas evolution had ceased, 2,4-dichloropyrimidine (3-1, 0.5 g, 3.36 mmol) was added. The mixture was heated to 50° C. After 18 hours the mixture was cooled to room temperature, quenched with saturated NH4Cl, and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (50% EtOAc/hexanes) gave 2-chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine as a gum. 1H-NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.38 Hz, 1H), 7.80 (s, 1H), 7.45 (m, 5H), 7.25 (s, 1H), 6.68 (d, J=5.38 Hz, 1H).

Provenance & Evidence