Acetic Anhydride → HCID 66672882, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(4-amino-3-methylphenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (2.10 g, 6.27 mmol) and sodium acetate (3.10 g, 31.3 mmol) in chloroform (80 mL) at room temperature was added acetic anhydride (3.0 mL, 31.3 mmol) and stirred for 15 min. The reaction mixture was warmed to 75° C. and added drop-wise isoamyl nitrite (5.10 g, 38 mmol) then stirred at 65° C. for 18 h. The reaction mixture was cooled to room temperature and washed with water (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The solution was dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, ethyl acetate/hexanes 1:2) to afford 1-acetyl-4-(1-acetyl-1H-indazol-5-yl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (1.06 g, 40%). MS (EI) for C24H22N4O4: 431 (MH+).

Provenance & Evidence