N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine → HCID 178487400, compound

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Reaction Steps

4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrimidin-2-amine was synthesized according to General Procedure E except N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine and 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine were used. 4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrimidin-2-amine 179 was isolated as a yellow solid. M.p.=130-133° C. 400 MHz 1H NMR (DMSO-d6) δ: 13.07 (br s, 1H), 8.39 (m, 3H), 7.98 (m, 2H), 7.73 (s, 1H), 7.27 (s, 1H), 6.91 (s, 1H), 6.85 (s, 2H), 6.44 (m, 1H), 4.02 (s, 3H), 3.80-3.76 (m, 8H), 3.41-3.39 (m, 4H), 2.95 (m, 2H), 2.84 (m, 2H); Experimental Elemental Analysis (1.73 equivalents of water and 0.38 equivalent of diethyl ether)=56.44% C, 4.74% H, 16.68% N; Calculated Elemental Analysis 56.44% C, 5.50% H, 16.68% N; LCMS (m/z): 697 [M+H].

Provenance & Evidence