Sodium Iodide → 5-Benzyl-3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one

Participants

Reaction Steps

A suspension of the compound of Example 1 Step 2 (1.8 g, 9.3 mmol) in anhydrous THF (40 mL) at room temperature was treated with 1M lithium hexamethyldisilazide (13.9 mL, 13.9 mmol) and stirred for 1 h. The mixture was then treated with benzylbromide (2.37 g, 1.65 mL, 13.9 mmol) and NaI (0.15 g, 1.0 mmol). The mixture was stirred at 50° C. for 40 h, then cooled to room temperature. The mixture was partitioned between ether and brine and the organic phase was washed with water. The organic phase was concentrated under vacuum and purified by flash chromatography on SiO2 (15% EtOAc/Hexane) to afford the desired product as a white solid (540 mg, 20%); 1H NMR (DMSO-d6) δ 7.35 (m, 5H), 5.41 (s, 2H), 2.79 (t, J=7.5 Hz, 2H), 2.53 (s, 3H), 1.72 (q, J=7.5 Hz, 2H), 0.90 (t, J=7.5 Hz, 3H); LC/MS (ESI): 284 (M+H)+.

Provenance & Evidence