Hydrochloric Acid → HCID 59363802, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 2,4-dichloro-6-(2-(isopentyloxy)phenyl)pyrimidine (100 mg, 0.32 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (91 mg, 0.35 mmol), Pd(dppf)Cl2 (3 mol %), 1 M NaHCO3 (0.3 mL), and THF (5 mL). The reaction mixture was heated to 70° C. for 2 hours. The reaction mixture was allowed to cool down to the room temperature, and 4 mL of conc. HCl was slowly added. The resulting slurry was heated to 100° C. for an additional 5 hours. The mixture was cooled down to room temperature, filtered, and concentrated under reduced pressure. The product was purified by preparative HPLC to result in 5-(6-{2-[(3-methylbutyl)oxy]phenyl}-2-oxo-1,2-dihydropyrimidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one. 1H NMR (400 MHz, d6-DMSO): δ 10.95 (s, 2H), 7.81-7.75 (m, 3H), 7.53 (t, 1H), 7.20 (d, 1H), 7.14-7.05 (m, 2H), 4.08 (t, 2H), 1.80-1.60 (m, 3H), 0.85 (s, 6H). MS (EI) for C22H22N4O3: 391 (MH+).

Provenance & Evidence