Potassium Hydroxide → HCID 90415973, compound

Participants

Reaction Steps

3,5-Diamino-N-(4-methoxy-3-pyridyl)-1H-pyrazole-4-carboxamide 9 (250 mg, 1.007 mmol), 1-allyloxy-3-(1,3-dioxolan-2-yl)propan-2-one (187.5 mg, 1.007 mmol) and KOH (5.650 mg, 0.1007 mmol) were suspended in dry EtOH (5 mL) and stirred at RT for 2 hr. The light brown suspension was filtered and the collected solid was purified by column chromatography on silica (7.5% MeOH in DCM, ˜75 mL) to give the desired Compound I-O-55 as a light yellow solid (206.5 mg, 58% Yield). LC-MS (M+H)+ 355.2; 1H NMR (500 MHz, DMSO-d6) δ 10.19 (s, 1H), 9.52 (s, 1H), 8.95 (d, J=6.9 Hz, 1H), 8.21 (d, J=5.5 Hz, 1H), 7.16 (d, J=5.5 Hz, 1H), 7.09 (d, J=6.9 Hz, 1H), 6.62 (s, 2H), 6.01 (ddt, J=17.3, 10.6, 5.4 Hz, 1H), 5.37 (dq, J=17.3, 1.8 Hz, 1H), 5.24 (ddt, J=10.5, 2.0, 1.3 Hz, 1H), 4.71 (s, 2H), 4.18 (dt, J=5.4, 1.5 Hz, 2H), 4.03 (s, 3H).

Provenance & Evidence