Potassium Carbonate → (S)-(2,4-Dichlorobenzyl)-[1-(4-trifluoromethyl-pyrimidin-2-yl)-pyrrolidin-3-yl]-amine

Participants

Reaction Steps

Stir a mixture of (S)-(2,4-dichlorobenzyl)-pyrrolidin-3-ylamine (266 mg, 1 mmol), 2-chloro-4-(trifluoromethyl)-pyrimidine (365 mg, 2 mmol) and polymer supported potassium carbonate (626 mg, 2 mmol) at 80° C. overnight. Filter away the polymer and pour the filtered reaction mixture onto a SCX-2 column. Elute with methanol and then elute with 2 M ammonia in methanol. Concentrate to give a residue and chromatograph on silica gel to give the title compound (258 mg, 66%). Prepare the hydrochloride salt essentially as described in EXAMPLE 1 to give the hydrochloride salt of the title compound. 1H NMR (400 MHz, MeOH-d4) δ 8.39 (2H, m), 7.71 (1H, d, J=8.56 Hz), 7.68 (1H, d, J=1.71 Hz), 7.51 (1H, dd, J=8.31, 1.96 Hz), 4.46-4.55 (2H, m), 4.19-4.26 (1H, m), 4.09-4.14 (1H, m), 3.89-3.98 (2H, m), 3.73 (1H, m), 2.63-2.70 (1H, m), 2.39-2.48 (1H, m), MS (ES): m/z=391 [M+].

Provenance & Evidence