Triethylamine → HCID 68524576, compound

Participants

Reaction Steps

A solution of palladium (II) acetate (82 mg, 0.37 mmol, 10 mol %) and tris (o-tolyl)phosphine (145 mg, 0.48 mmol) in anhydrous acetonitrile (40 mL) was sparged with argon for 5 minutes. Triethylamine (5.10 mL, 36.60 mmol) was added, followed by N-tert-butyl-2-[2-(3-chlorophenyl)-6-iodo-4-oxo-4H-quinazolin-3-yl]acetamide (INTERMEDIATE IV.12) (1.81 g, 3.66 mmol) and 3-buten-1-ol (1.57 mL, 18.30 mmol). The resultant mixture was heated at reflux temperature for 18 h. The resultant green suspension was concentrated in vacuo, and the residue was treated with ethyl acetate (100 mL) and filtered. The black precipitate was washed with ethyl acetate (2×50 mL), and the combined filtrates were washed with 1N HCl (aq.) (2×100 mL), brine (100 mL), dried (MgSO4) and concentrated to give the crude product as yellow-orange foam. Trituration with ether provided N-tert-butyl-2-[2-(3-chlorophenyl)-6-(4-hydroxybut-1-enyl)-4-oxo-4H-quinazolin-3-yl]acetamide (766 mg, 1.74 mmol, 48%) as an off-white powder.

Provenance & Evidence