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aReagents and conditions: (a) (i) n-BuLi, THF, −78 °C, 40 min; (ii) 1-benzylpiperidin-4-one, THF, −78 °C; (b) SOCl2, 0 °C, 2 h; (c) (i) HCO2NH4, 10% Pd/C, CH3OH, reflux; (ii) 4.0 M HCl solution in 1,4-dioxane, CH3CN, rt, 2 h; (d) methyl 2-chloro-6-methylpyrimidine-4-carboxylate, i-Pr2NEt Et3N, DMF, 60 °C, 16 h; (e) (i) LiOH·H2O, H2O, THF, rt, 16 h; (ii) 2 N aq HCl.
