Hydrochloric Acid → (1R)-N2-[6-(3-Chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-1-(4-fluoro-phenyl)-ethane-1,2-diamine

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Reaction Steps

A solution of (R,R)-2-methyl-propane-2-sulfinic acid [2-[6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-1-(4-fluoro-phenyl)-ethyl]-amide (0.172 g, 0.337 mmol) in MeOH (5 mL) was added HCl (4 N in dioxane, 0.34 mL) at rt. After 30 min, the reaction mixture was purified directly via reverse phase chromatography. The desired fractions were then free-based by washing with sat. aq. NaHCO3 (2×30 mL) and extracting with EtOAc (2×25 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (75 mg, 54%) as a white solid. MS (ESI+): calcd for C19H15ClF4N4 m/z 410.09. found 411.1 (M+H)+. 1H NMR (CDCl3): 8.60 (s, 1H), 8.05 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.35 (dd, J=8.6, 5.3 Hz, 2H), 7.05 (t, J=8.6 Hz, 2H), 6.66 (s, 1H), 5.89 (s, 1H), 4.27 (s, 1H), 3.76-3.64 (m, 1H), 3.59-3.50 (m, 1H), 3.03-2.85 (m, 2H).

Provenance & Evidence