Sodium Carbonate → HCID 135589862, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-6-(2-(isopentyloxy)phenyl)pyrimidine (0.32 mmol, 100 mg) in 5 mL of THF was added 4-hydroxyphenylboronic acid (0.33 mmol, 46 mg), Pd(OAc)2 (4 mol %, 10 mg) and PPh3 (8 mol %, 9 mg) followed by Na2CO3 (1M, 1.20 mL). The reaction was heated to 60° C. for 2 hours, then concentrated in vacuo. 8 mL of conc. HCl was added to the reaction mixture which was heated to 90° C. Once the hydrolization was complete, the reaction was concentrated in vacuo. The residue was dissolved in methanol and passed through a stratosphere SPE cartridge (Polymer Labs) to remove Pd. Purification by HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate), followed by concentration in vacuo and lyophilization gave the title compound 4-(4-hydroxyphenyl)-6-(2-(isopentyloxy)phenyl)pyrimidin-2(1H)-one (35 mg, 30% yield). 1H NMR (400 MHz, d-4-MeOH): 8.03-7.97 (m, 2H), 7.67-7.63 (m, 1H), 7.56-7.51 (m, 1H), 7.22-7.18 (m, 2H), 7.15-7.10 (m, 1H), 6.93-6.90 (d, 2H), 4.17 (t, 2H), 1.85-1.70 (m, 3H), 0.95 (s, 3H), 0.93 (s, 3H). MS (EI) for C21H22N2O3: 351 (MH+).

Provenance & Evidence