Benzimidazole → HCID 15549639, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of NaH (0.548 mg, 22.8 mmol), benzimidazole (0.52 g, 21.3 mmol) and 4-chloro-2-methylthiopyrimidine (2.48 mL, 21.3 mmol) in 30 mL of DMF was heated to 100° C. for 30 min. The reaction was quenched with H2O and extracted with EtOAc. The combined organic fractions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography (silica, 0-10% MeOH:CH2Cl2) to give 1.99 g of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.69 (s, 1H); 8.64 (d, J=5.5 Hz, 1H); 8.22 (dd, J=1.4, 7.3 Hz); 7.89 (dd, J=1.6, 7.3 Hz); 7.44 (m, 2H); 7.23 (d, J=5.7 Hz, 1H); 2.69 (s, 3H).

Provenance & Evidence