Tetrahydrofuran → HCID 86705397, compound

Participants

Reaction Steps

9-Acetyl-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 81, 254 mg, 0.76 mmol), THF (1.3 mL) and 2 M trimethyl(trifluoromethyl)silane in THF (0.45 mL, 0.91 mmol) were combined and stirred for 10 minutes. A 2 M solution of tetrabutylammonium fluoride in THF (75 μl, 0.08 mmol) was added and stirring was continued for 3 days. Additional trimethyl(trifluoromethyl)silane (0.45 mL, 0.91 mmol) and tetrabutylammonium fluoride (75 μl, 0.08 mmol) was added and the mixture was stirred for 4 h. The reaction mixture was diluted with aqueous sodium bicarbonate (5 mL) and extracted with EtOAc (2×10 mL). The combined extracts were concentrated under vacuum. Purification (FCC, SiO2, 10 to 100%, EtOAc/hexanes) afforded the title compound (154 mg, 48%) as a white powder. 1H NMR (400 MHz, CDCl3+DMSO-d6) δ 3.27 (s, 3H), 4.80 (q, J=6.90 Hz, 1H), 5.24 (s, 2H), 6.33 (d, J=8.66 Hz, 2H), 7.05 (d, J=8.53 Hz, 2H), 7.91 (s, 1H), 8.32 (s, 1H), 8.39 (s, 1H). [M+H]=406.1.

Provenance & Evidence