Ammonia → (S)-2-[3-(2,4-Dichlorobenzylamino)-pyrrolidin-1-yl]-pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Add zinc cyanide (104 mg, 0.88 mmol) and tetrakis(triphenylphosphine) palladium(0) (209 mg, 0.18 mmol) to a stirred solution of (S)-(2,4-dichlorobenzyl)-[1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-yl]-amine (359 mg, 0.89 mmol) in N,N-dimethylformamide (5 mL). Heat at 65° C. for 4 hours. Cool to room temperature and add 2 M aqueous ammonia solution (30 mL). Extract with ethyl acetate (3×50 mL), extract the combined organic layers with water (5×50 mL) followed by saturated aqueous sodium chloride (50 mL). Concentrate to give a residue. Dissolve the residue in dichloromethane, filter, and concentrate to give a residue. Chromatograph the residue on silica gel to give the title compound as a white solid (111 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 8.50 (2H, m), 7.32-7.40 (2H, m), 7.20-7.27 (1H, m), 3.86-3.94 (2H, m), 3.75-3.83 (2H, m), 3.63-3.71 (1H, m), 3.48-3.55 (2H, m), 2.20 (1H, m), 1.95 (1H, m); MS (ES): m/z=348 [M+].

Provenance & Evidence