Hydrochloric Acid → HCID 178496114, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 4-(3-methyl-1-acetyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (2.50 g, 6.2 mmol), MeOH (60 mL) and 10 ml of 4 N HCl in dixoane (Aldrich). The mixture was heated at 60° C. overnight. The reaction was concentrated, and the residue was submitted to preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate) to result in 4-(3-methyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (1.32 g). 1H NMR (400 MHz, d6-DMSO): δ 12.90 (s, br, 1H), 11.75 (s, br, 1H), 8.60 (s, 1H), 8.15 (d, 1H), 7.75 (d, 1H), 7.60-7.45 (m, 3H), 7.25-7.10 (m, 2H), 4.20 (t, 2H), 3.75 (t, 2H), 3.40 (s, 3H), 2.60 (s, 3H). MS (EI) for C21H20N4O3: 377 (MH+); and 6-{2-[(2-hydroxyethyl)oxy]phenyl}-4-(3-methyl-1H-indazol-5-yl)pyrimidin-2(1H)-one (250 mg) 1H NMR (400 MHz, d6-DMSO): δ 8.88 (s, 1H), 8.09 (d, 1H), 7.80-7.45 (m, 4H), 7.35-7.05 (m, 2H), 4.23 (t, 2H), 3.80 (t, 2H), 2.40 (s, 3H). MS (EI) for C20H18N4O3: 363 (MH+).

Provenance & Evidence