Methyl iodide → HCID 22417671, compound

Participants

Reaction Steps

Potassium bis(trimethylsilyl)amide (41 mL, 0.5M in toluene, 20.4 mmol) was added to a solution of 2-cyano-5,6-dimethylpyridine from Example 1, Step 2 (2.45 g, 18.5 mmol) and hexamethylphosphoric triamide (9.7 mL, 55.6 mmol) in dry THF (30 mL) at -78° C. After stirring 30 minutes, MeI (5.77 mL, 92.7 mmol) was added and the reaction mixture stirred 45 minutes at -78° C. Saturated aq. NH4Cl was added, the mixture was extracted with EtOAc (3×), the organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (from 15:15:70 to 20:20:60 of Et2O: CH2Cl2 : hexanes) to give 1.2 g (44%) of the title compound.

Provenance & Evidence