Chlorotrimethylsilane → HCID 67288108, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of lithium borohydride (1055 μL, 2.11 mmol) (in 2 mL of THF) was added chlorotrimethylsilane (535 μL, 4.22 mmol) dropwise. After stirring for 15 minutes, Argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-6-Cyclopropyl-N,N-dimethyl-3-(2-nitrovinyl)pyridin-2-amine (123 mg, 0.527 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 3-(2-aminoethyl)-6-cyclopropyl-N,N-dimethylpyridin-2-amine (107 mg, 0.521 mmol, 98.8% yield).

Provenance & Evidence