Acetic Acid → 4-amino-5-(2-methylprop-1-enyl)quinazolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(2-cyano-3-(2-methylprop-1-enyl)phenyl carbamoyl)benzamide (Example 150a) (0.133 g, 0.416 mmol) in EtOH (3 mL) was treated with a solution of NaOH (2 M, 0.416 mL, 0.832 mmol) at room temperature. The obtained mixture was heated at 90° C. for 30 min, cooled to room temperature and neutralized with 10% AcOH. The precipitated product was collected by filtration to give 69.0 mg (77%) of 4-amino-5-(2-methylprop-1-enyl)quinazolin-2(1H)-one as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.60 (d, J=1.2 Hz, 3H), 1.93 (d, J=1.2 Hz, 3H), 6.58 (s, 1H), 6.67 (broad s, 1H), 6.73 (m, 1H), 7.05 (m, 1H), 7.48 (m, 1H), 7.93 (broad s, 1H), 10.72 (broad s, 1H). MS 216 (MH+).

Provenance & Evidence