Hydrochloric Acid → HCID 11587369, compound

Participants

Reaction Conditions

Reaction Steps

Part B. A 10 mL microwave tube is charged with 4-chloro-6-m-tolyl-pyrimidine (45.7 mg, 0.22 mmol), 4-carboxyphenylboronic acid (39.2 mg, 0.23 mmol), (235.3 mg, 2.22 mmol), Na2CO3 (70.6 mg, 0.67 mmol), tetrabutylammonium iodide (83.0 mg, 0.22 mmol), palladium acetate (0.5 mg, 2.2×mmol) and 2 mL of water. The reaction mixture is heated to 150° C. at 60 w, 250 psi in a microwave reactor for 10 min. The reaction mixture is added to 5 mLl of 6 N HCl and extracted with ethyl acetate (10 mL). The organic portion is washed with saturated NaHCO3 and brine, dried (MgSO4), and concentrated on a rotary evaporator. The oily residue is suspended in ethyl acetate/hexanes (1:1) to provide 9.8 mg (15.1% yield) of white powder as the desired product, m.p. 211-213° C. 1H NMR (300 MHz, DMSO-d6): δ 9.31 (1H, s), 8.66 (1H, s), 8.46 (2H, d, J=8.3 Hz), 8.20 (1H, s), 8.15 (1H, dd, J=8.0, 1.2 Hz), 8.09 (2H, d, J=8.3 Hz), 7.45 (1H, t, J=7.7 Hz), 7.38 (111, dd, J=7.7, 1.0 Hz). MS (ES+): m/e 291.58.

Provenance & Evidence