Water → HCID 86714786, compound

Participants

Reaction Steps

To a solution of (R)-2-chloro-N-(2,2-dimethylhex-5-en-3-yl)-5-fluoropyrimidin-4-amine, 188a, (0.140 g, 0.543 mmol) in THF (10 mL) and H2O (10 mL) was added osmium tetraoxide (0.138 g, 0.014 mmol) and 4-methylmorpholine-4-oxide (0.085 mL, 0.815 mmol). The reaction mixture was stirred at room temperature for 2.5 hours. The mixture was diluted with aqueous saturated Na2S2O3. The resulting mixture was stirred for 20 minutes and extracted with EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (MeOH/CH2Cl2) to afford 90 mg of the first diastereomer, 189a, and 65 mg of the second diastereomer, 190a.

Provenance & Evidence