Sodium Hydroxide → HCID 77230715, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-8-carboxylate (2.00 g; 9.17 mmol; 1.00 eq.) and benzyltriethylammonium chloride (4.18 g, 18.33 mmol) in dry CH3CN (5 mL) was treated with DIEA (1.75 mL, 10.1 mmol) and stirred as POCl3 (7.3 mL, 80.2 mmol) was slowly added to the flask. The contents were warmed to 90° C. for 30 min, cooled to ˜50° C., and slowly poured into a 2N NaOH (80 mL, 160 mmol) and water (80 mL) that was cooling in an acetone/dry-ice bath (ice formed in the flask). The off-red solid that precipitated was filtered, washed with 10% aqueous K2CO3 (15 mL), and dried under vacuum to afford 1 (1.35 g; 62% yield). LC-MS [236.8 (M+1)]

Provenance & Evidence