2‐(Pyrimidin‐5‐yl)benzaldehyde 1

Abstract

[640769-71-7] C11H8N2O (MW 184.20) InChI = 1S/C11H8N2O/c14-7-9-3-1-2-4-11(9)10-5-12-8-13-6-10/h1-8H InChIKey = JPSJBEALHNYNBL-UHFFFAOYSA-N (meta-selective transient directing group) Physical Appearance: white solid. Melting Point: 168–170 °C. Solubility: soluble in most organic solvents such as hexafluoroisopropanol (HFIP), dichloromethane, chloroform, ethyl acetate, and acetonitrile. Analytical Data: 1H NMR (500 MHz, CDCl3) δ (ppm).10.01 (s, 1H), 9.29 (s, 1H), 8.79 (s, 2H), 8.08 (dd, J = 7.7, 1.1 Hz, 1H), 7.76 (td, J = 7.5, 1.3 Hz, 1H), 7.67 (t, J = 7.5 Hz, 1H), 7.42 (d, J = 7.6 Hz, 1H). 13C NMR (126 MHz, CDCl3) δ (ppm). 190.63, 158.04, 156.71, 137.22, 134.19, 133.77, 132.28, 131.31, 130.57, 129.61. IR (thin film, cm−1): 1000, 1055, 1200, 1266, 1355, 1416, 1549, 1597, 1654, 1689, 2764, 2869, 2923, 3042. Preparative Method: a clean, oven-dried screw cap reaction tube with previously placed magnetic stir-bar was charged with 5-bromopyrimidine (1 equiv), (2-formylphenyl)boronic acid (1.25 equiv), Pd(OAc)2 (2 mol %), SPhos (4 mol %), and K3PO4 (2 equiv). The cap was fitted with a rubber septum, and the reaction tube was evacuated and backfilled with nitrogen, and this sequence was repeated three additional times. Under the positive flow of nitrogen, 15 mL THF was added to the reaction mixture. The reaction mixture was vigorously stirred at 80 °C temperature for 24 h. Next, the reaction was allowed to cool at room temperature and dried using rotary evaporator. The reaction mixture was extracted three times with ethyl acetate and brine solution. The organic layer was collected and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The crude mixture was purified by column chromatography using silica gel and petroleum-ether/ethyl acetate as the eluent.1 Handling, Storage, and Precautions: The compound is stable under atmospheric conditions and does not undergo decomposition over a period of time when stored in a sealed container. It is safe to handle, without any risk of burns or inflammation.