Acetic Acid → HCID 68089182, compound

Participants

Reaction Steps

To 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (Int-8b, 0.15 g, 0.3 mmol) in EtOH (10 mL) was added morpholine (0.12 mL, 1.4 mmol) and AcOH (0.2 mL), and the resulting mixture was stirred at room temperature for 15 minutes. NaBH3CN (0.12 g, 2.0 mmol) in EtOH (1.5 mL total) was then added and the reaction mixture was stirred at room temperature for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. Saturated NaHCO3 solution (˜20 mL) was added and the mixture was stirred for 30 minutes. The mixture was transferred to a separatory funnel with CH2Cl2 (30 mL). H2O (10 mL) and brine (20 mL) were then added. Organics were extracted with CH2Cl2 (4×30 mL), dried (Na2SO4) and concentrated in vacuo to give crude product (0.2 g). LCMS: 2.01 mins, m/z=635.3 (MH+).

Provenance & Evidence