Formamidine acetate → 4-[4-(4-Fluorophenyl)-1-pyrrolidin-3-yl-1H-imidazol-5-yl]pyrimidine

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Reaction Steps

tert-Butyl 3-[4-(4-fluorophenyl)-5-pyrimidin-4-yl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C19, prepared according to the general procedure for the synthesis of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C17) in Example 7, except that formamidine acetate was used in place of guanidine hydrochloride) was converted to the product using conditions similar to those employed for transformation of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C17) to 4-[4-(4-fluorophenyl)-1-pyrrolidin-3-yl-1H-imidazol-5-yl]pyrimidin-2-amine (C18) in Example 7. The product was obtained as a solid. Yield: 1.58 g, 5.11 mmol, 70%. LCMS m/z 310.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.16 (m, 1H), 2.37 (m, 1H), 3.02 (m, 1H), 3.09 (dd, J=12.2, 4.6 Hz, 1H), 3.21 (m, 1H), 3.3 (m, 1H, assumed; obscured by solvent signal), 5.32 (m, 1H), 7.09 (dd, J=8.6, 8.6 Hz, 2H), 7.26 (d, J=5.2 Hz, 1H), 7.38 (dd, J=8.3, 5.5 Hz, 2H), 8.15 (s, 1H), 8.63 (d, J=5.5 Hz, 1H), 9.28 (s, 1H).

Provenance & Evidence