Hydrochloric Acid → N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine

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Reaction Steps

Compound (109) was dissolved in methanol (2 mL) and charged with HCl (1 mL, 4 M solution in dioxane). The resulting mixture was stirred at room temperature for 16 h. It was then filtered and dried under high vacuum to afford N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine (110) as a yellow solid (0.125 g). M.p.=138-140° C. 400 MHz 1H NMR (DMSO-d6) δ: 9.36 (br s, 2H), 8.44-8.43 (m, 2H), 8.02 (d, J=9.0 Hz, 1H), 7.86 (s, 1H), 7.52 (s, 1H), 7.43 (s, 1H), 7.31 (d, J=6.3 Hz, 1H), 6.92-6.82 (m, 3H), 3.97 (s, 3H), 3.73-3.68 (m, 8H), 3.41-3.31 (m, 8H), 2.89 (m, 2H); Experimental Elemental Analysis (2.9 equivalents of HCl)=57.53% C, 5.90% H, 11.37% N; Calculated Elemental Analysis 57.54% C, 5.98% H, 11.57% N; LCMS (m/z): 500 [M+H].

Provenance & Evidence