tert-Butanol → HCID 86664794, compound

Participants

Reaction Steps

To 3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5-vinylpyrazolo[1,5-a]pyrimidin-7-amine (1.3 g, 2.2 mmol) in 1,4-doixane (20 mL) was added 2.5 wt % OsO4 in t-BuOH (4.9 g, 0.1 mmol), 2,6-lutidine (1.1 mL, 9.0 mmol) and H2O (3 mL) and the resulting mixture was stirred at room temperature for 1 hour. NaIO4 (1.9 g, 8.9 mmol) was then added and stirring at room temperature was continued for 16 hours. LC/MS analysis at this time showed no starting material or diol intermediate present and confirmed full conversion to product. Saturated Na2S2O3 solution (30 mL) was added and the mixture stirred for 10 minutes. The reaction was transferred to a separatory funnel with CH2Cl2 (30 mL) and H2O (30 mL) and organics were extracted with CH2Cl2 (4×40 mL), dried (Na2SO4) and concentrated in vacuo to give 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde as a brown solid (1.3 g, 2.2 mmol, 100%). LC/MS: 2.92 mins, m/z=568.3 (MH+).

Provenance & Evidence