Potassium Carbonate → 1-(5-Nitro-2-pyrimidinyl)-3-piperidinol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of piperidin-3-ol (0.333 g, 3.29 mmol) and 2-chloro-5-nitropyrimidine (0.500 g, 3.13 mmol) in DMF (8 mL) was added K2CO3 (1.04 g, 7.52 mmol). The resulting yellowish suspension was stirred at 70° C. for 1.5 h. After this time, the reaction was determined to be complete by LC/MS. The reaction mixture was cooled to rt, then partitioned between water and EtOAc. The separated aqueous phase was extracted with EtOAc (2×). The combined EtOAc extracts were washed with water (1×), saturated aqueous NaCl (2×), dried over Na2SO4, filtered and concentrated. The resulting residue was dried under vacuum for 30 min to afford the desired product 1-(5-nitropyrimidin-2-yl)piperidin-3-ol (536 mg, 2.391 mmol, 76% yield) as a yellow solid. Anal. Calcd. for C9H12N4O3 m/z 224.2, found: 225.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 9.17-8.91 (m, 2 H), 4.20 (dd, J=13.14, 3.03 Hz, 1 H), 4.03 (ddd, J=13.07, 7.14, 3.79 Hz, 1 H), 3.96-3.74 (m, 2 H), 2.95 (s, 1 H), 2.11-1.87 (m, 2 H), 1.81-1.50 (m, 3 H).

Provenance & Evidence