2-Amino-5-cyanopyridine → HCID 57504560, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylaluminium (2M in toluene) (0.795 mL, 1.59 mmol) was added dropwise to a stirred solution of 6-aminonicotinonitrile (165 mg, 1.38 mmol) in toluene (5 mL) cooled to 0° C., over a period of 1 minute under nitrogen. The resulting solution was stirred at 0° C. for 20 minutes. A solution of (2S)-methyl 5-(tert-butyldimethylsilyloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)pentanoate (Intermediate O2) (680 mg, 1.38 mmol) in toluene (5 mL) was added dropwise. The resulting solution was stirred at 0° C. for 10 minutes allowed to warm to ambient temperature and then heated at reflux for 18 hours. The reaction mixture was allowed to cool to r.t. and concentrated. The residue was diluted with ethyl acetate and treated with 1M citric acid (2 ml). The layers were separated and the organics were washed with water and brine, dried (MgSO4) and evaporated to afford the product (797 mg) which was used without further purification. m/z (ES−) (M−H)−=577.45; HPLC tR=3.29 min.

Provenance & Evidence