Triethylamine → 4,6-Dichloro-2-propylquinazoline

Participants

Reaction Steps

Preparation D10, Step 3: 6-Chloro-2-propylquinazolin-4-ol (810 mg, 3.64 mmol, 1 eq), phosphorus oxychloride (3.30 mL, 35.1 mmol, 9.64 eq) and triethylamine (1.63 mL, 11.7 mmol, 3.21 eq) were mixed at room temperature then refluxed for 2.5 hours. The reaction was stripped 3 times from methylene chloride. The residue was dissolved in methylene chloride (25 mL) and rinsed 3 times with saturated sodium bicarbonate (25 mL), 1× with water (25 mL). The organic layer was dried (sodium sulfate) and stripped to an amber oil. Purified over silica gel in 9:1 hexanes/ethyl acetate to give 4,6-dichloro-2-propylquinazoline (510 mg) as a light-amber solid. Yield=58%. 1H NMR (400 MHz) (CD3OD) □ 7.98 (s, 1H); 7.98 (d, 1H, J=7 Hz); 7.93 (d, 1H, J=7 Hz); 3.00 (t, 2H, J=7 Hz); 1.90 (t of q, 2 H, J=7 Hz); 1.00 (t, 3H, J=7 Hz).

Provenance & Evidence