Triethylamine → HCID 59860369, compound

Participants

Reaction Steps

Dissolve 1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-ylamine hydrochloride (60 mg, 0.22 mmol) in methanol (10 mL) and dichloromethane (1 mL). Add triethylamine (100 μL, 0.72 mmol) and 4-bromo-2-fluorobenzaldehyde (87 mg, 0.43 mmol) and stir overnight at room temperature. Add sodium borohydride (25 mg, 0.66 mmol) and stir 1 h. Dilute the mixture with methanol and pour onto a column of Dowex® 50wx4-200. Wash with methanol, then elute with 10% triethylamine in methanol. Concentrate and chromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate:hexanes to give the title compound as a residue. Dissolve the residue in methanol and add 1 N HCl in methanol (0.75 mL). Concentrate and dry in a vacuum oven at 60° C. overnight to give the title compound as its hydrochloride salt, as a white solid (80 mg, 80%). 1H NMR (400 MHz, MeOH-d4) 8.45 (s, 2H), 7.57-7.52 (m, 3H), 4.42-4.34 (m, 2H), 4.15-4.09 (m, 1H), 4.04-3.99 (m, 1H), 3.87-3.77 (m, 2H), 3.69-3.62 (m, 1H), 2.63-2.54 (m, 1H), 2.36-2.27 (m, 1H), MS (ES): m/z=429 [M+H].

Provenance & Evidence