Hydrochloric Acid → 4-[1-Azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amine

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Reaction Steps

To a solution of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C4) (2.1 g, 5.1 mmol) in methanol (10 mL) was added aqueous hydrochloric acid (5 N, 30 mL) and the reaction was stirred for 2 hours at room temperature. The solution was concentrated and the residue was diluted with water (100 mL) and ethyl acetate (100 mL). After adjusting the mixture to pH=9 with aqueous ammonia, the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give the product as a solid. Yield: 1.1 g, 3.5 mmol, 69%. LCMS m/z 311.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 3.95 (br d, J=7.5 Hz, 4H), 5.51 (m, 1H), 6.38 (br d, J=5.2 Hz, 1H), 7.10 (br dd, J=8.5, 8.5 Hz, 2H), 7.44 (br dd, J=8, 5 Hz, 2H), 8.10 (br d, J=5.0 Hz, 1H), 8.21 (br s, 1H).

Provenance & Evidence