Dichloromethane → HCID 18779722, compound

Participants

Reaction Steps

3-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-1-ol from step 1 (2.4 g, 9.9 mmol) was dissolved in CH2Cl2 (100 mL) and treated with trimethylsilylcyanide (1.3 ml, 9.9 mmol). The reaction mixture was stirred for 5 min. at room temperature. The mixture was then treated with dimethylcarbamyl chloride (910 μl, 9.9 mmol) and stirred at room temperature for 15 hours. HPLC analysis showed that the reaction had not gone to completion. More trimethylsilylcyanide (264 μl, 1.98 mmol) and dimethylcarbamyl chloride (910 μl, 9.9 mmol) were added and the reaction mixture was heated to 75° C. for 3.5 hrs. The reaction was cooled to room temperature and saturated NaHCO3 (50 mL) was added. The mixture was separated and the water layer was extracted with CH2Cl2 (2×40 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography [2% MeOH(5% NH4OH)/CH2Cl2) to yield a mixture of of 3-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridine-2-carbonitrile and 5-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridine-2-carbonitrile (10:1).

Provenance & Evidence