Hydrochloric Acid → 6-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine

Participants

Reaction Steps

Use a method similar to the General Procedure 6-5 to react 6-(tert-butylthio)nicotinonitrile (4.4 g, 22.7 mmol) in anhydrous THF (25 mL) with 1M BH3-THF complex in THF (25 mL, 25 mmol). Add 5M aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Extract into EtOAc, wash with brine, dry over MgSO4 and concentrate in vacuo to give an orange solid. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (2.74 g, 61%). MS (ES+) m/z: 197 (M+H)+.

Provenance & Evidence