2-Bromopyrimidine → 4-(1-Pyrimidin-2-ylpiperidin-4-ylamino)benzoic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-Bromopyrimidine (0.016 g, 0.1 mmol) was added to a solution of (49) (0.032 g, 0.12 mmol) in tert-butyl alcohol (2 mL) at 25° C. The mixture was heated to 90° C. and was maintained at that temperature for 12 h. The reaction mixture was then cooled to room temperature and concentrated to a yellow oily residue. Purification of the residue by flash column chromatography (gradient elution 0 to 20% EtOAc in hexanes) provided the title compound (0.032 g, 89%): TLC (Rf =0.41; 40% EtOAc/hexanes); 1H NMR (CDCl3) δ 8.29 (d, 2H, J=4.7), 7.80 (d, 2H, J=8.8), 6.54 (d, 2H, J=8.8), 6.46 (t, 1H, J=4.7), 4.66 (d, 2H, J=13.7), 3.96 (d, 1H, J=7.8), 3.63 (m, 1H), 3.13 (t, 2H, J=12.0), 2.12 (d, 2H, J=12.0), 1.54 (s, 9H), 1.43 (m, 2H); 13C NMR (CDCl3) δ 166.1, 161.6, 157.8, 150.3, 131.5, 120.5, 111.8, 109.8, 79.9, 50.1, 42.6, 32.1, 28.3; HRMS (FAB) m/z 355.2126 (M+H)+ (C20H26N4O2 requires 355.2134).

Provenance & Evidence