Benzimidazole → HCID 18375460, compound

Participants

Reaction Steps

To a suspension of NaH (76 mg) in DMF (2 mL) was added benzimidazole, and this was followed by addition of 2-ethylthio4-chloro-6-propylpyrimidine dissolved in DMF (3 mL). The reaction mixture was then placed in a 100° C. oil bath. After 1 h, the reaction was cooled to room temperature, quenched with 5 mL of water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl and dried (anhydrous Na2SO4). Removal of solvent followed by purification on silica gel column (9% acetone/hexane) provided 390 mg of the title compound. Mass spectrum (CI) 298 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.69 (s, 1H); 8.17 (d, J=7.6 Hz, 1H); 7.88 (d, J=7.8 Hz, 1H); 7.42 (m, 2H); 7.05 (s, 1H); 3.27 (q, J=7.4 Hz, 2H); 2.78 (t, J=7.5 Hz, 2H); 1.85 (m, 2H); 1.49 (t, J=7.3 Hz, 3H); 1.05 (t, J=7.3 Hz, 3H).

Provenance & Evidence