Triethylamine → 4-Ethoxy-quinazoline-6-carbaldehyde

Participants

Reaction Steps

The mixture of 6-bromo-4-ethoxy-quinazoline (example 10a, 506 mg, 2 mmol,), diphenylpropyl phosphine (45.6 mg, 0.2 mmol), palladium acetate (44.8 mg, 0.2 mmol) and triethyl amine (505 mg, 5 mmol) in anhydrous N,N-dimethylformamide (DMF) (25 ml) was charged with carbon monoxide at 75 psi. After the above reaction mixture was stirred at room temperature for 15 min, the carbon monoxide was released, and trihexylsilane (1140 mg, 4 mmol) was added. The resulted reaction mixture was charged with carbon monoxide at 75 psi, and heated at 80° C. for 18 hr. After cooling the reaction to room temperature, dichlormethane was added. The resulted solution was extracted with water for 3 times. Organic layer was collected and concentrated to give a yellow solid. Flash chromatography (Merck silica gel 60, 230-400 mesh, 10%-40% ethyl acetate in hexane for 40 min) gave 4-ethoxy-quinazoline-6-carbaldehyde (256 mg, 66%) as a light yellow solid. LC-MS m/e 203 (MH+).

Provenance & Evidence