3-Bromo-1-propanol → HCID 18327323, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (239 mg, 9.94 mmol) was added to a solution of 2-(4-chlorophenoxymethyl)-8-methoxy-3H-quinazolin-4-one (3000 mg, 9.47 mmol) in DMF (20 mL) at room temeprature. The reaction mixture was stirred for 30 min, then 3-bromopropanol (1448 mg, 0.94 mL, 10.42 mmol) was added. The reaction mixture was heated at 80° C. for 17 h, cooled to room temperature and diluted with EtOAc. The organic solution was washed with water, sat'd aq NaCl, dried and concentrated. The crude residue was purified using SiO2-gel chromatography (50% EtOAc/hexanes) to give 1.1 g of the desired N-alkylated product. API-MS: 375 (M+1). 1H NMR (300 MHz, CDCl3): d 7.82 (d, 1 H), 7.4 (t, 1 H), 7.2 (m, 3 H), 7.9 (d, 2 H), 5.2 (s, 2 H), 4.36 (t, 2 H), 4.0 (s, 3 H), 3.58 (t, 2 H), 2.0 (t, 2 H).

Provenance & Evidence