Potassium Carbonate → 6,8-diiodo-2-(propylthio)-3-[(tetrahydro-2-furanyl)methyl]-4(3H)-quinazolinone

Participants

Reaction Steps

A mixture of the title compound of Step A (0.86 g, 1.67 mmol), n-propyl iodide (0.85 g, 5.02 mmol) and potassium carbonate (2.3 g, 16.7 mmol) was stirred in dimethylformamide (20 mL) at ambient temperature for approximately 4 h. The reaction mixture was then concentrated to dryness in vacuo and partitioned between 200 mL each of ethyl acetate and water. The organic phase was then separated, washed with saturated aqueous NaCl, and dried over Na2SO4. Concentration in vacuo provided 0.82 g of the title compound of Step B, a compound of the invention, as a solid melting at 108-111° C. 1H NMR (300 MHz, CDCl3): δ 1.10 (t,3H), 1.63-1.80 (m,1H), 1.80-2.14 (m,5H), 3.24-3.45 (m,2H), 3.70-3.80 (m,1H), 3.90-4.00 (m,1H), 4.10-4.21 (m,2H), 4.35-4.47 (m,1H), 8.44 (d,1H), 8.48 (d,1H).

Provenance & Evidence