3-Aminopyridine → HCID 5329431, compound

Participants

Reaction Steps

To a solution of 2-chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (3-2, 50 mg, 0.2 mmol), 3-aminopyridine (22 mg, 0.23 mmol), NaOtBu (26 mg, 0.27 mmol), 2-biphenyl-di-tert-butylphosphine (5 mg, 0.02 mmol) was added Pd(OAc)2 (2 mg, 0.01 mmol) at room temperature. After 72 hours the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 3-10% MeOH/CH2Cl2) gave the title compound as an off-white solid after trituration with Et2O/hexanes. 1H-NMR (500 MHz, CDCl3) δ 8.62 (d, J=1.95 Hz, 1H), 8.33 (d, J=5.37 Hz, 1H), 8.29 (d, J=4.40 Hz, 1H), 7.91 (d, J=7.08 Hz, 1H), 7.61 (d, J=1.22 Hz, 1H), 7.50 (m, 2H), 7.41 (m, 3H), 7.21 (m, 2H), 6.40 (d, J=5.37 Hz, 1H).

Provenance & Evidence