Benzimidazole → HCID 86758759, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (74 mg) in DMF (5 mL) at 0° C. was added benzimidazole (204 mg). The reaction mixture was stirred at 0° C. until gas evolution ceased, then stirred at room temperature until the mixture became homogeneous (ca. 10 min.). A solution of 2-[(S)-1-phenylethylamino]-4,6-dichloropyrimidine (412 mg) in DMF (2 mL) was added to the mixture, which was then placed in 100° C. oil bath for 1 h. The reaction mixture was cooled and carefully quenched with water. The layers were separated, and the aqueous layer was extracted CH2Cl2 (2×15 mL). Combined organic layers was washed with water and brine and dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and the crude product was purified by flash chromatography (1:5 EtOAc:hexanes) to give 330 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.21 (br s, 1H); 7.82 (d, J=7.5 Hz, 1H); 7.75 (br s, 1H); 7.45-7.28 (m, 7H); 6.8 (s, 1H); 5.92 (br s, 1H); 5.2 (br s, 1H); 1.62 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 350.2 (M+1).

Provenance & Evidence