Sodium Carbonate → 9-isopropyl-6-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-9H-purine

Participants

Reaction Steps

Compound 52B (165 mg, 0.84 mmol) in toluene (5 ml) was treated sequentially with 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (280 mg, 1.26 mmol), tetrakis(triphenylphosphine)palladium(0) (48.6 mg, 0.042 mmol) and sodium carbonate (2N aq.) (1.26 ml, 2.52 mmol). The reaction vessel was purged with nitrogen and heated at reflux overnight. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel eluting with a gradient of 0 to 5% MeOH in CH2Cl2: 1H NMR (300 MHz, DMSO-d6) δ ppm 8.92 (1H, s), 8.83 (2H, m), 8.74 (1H, s), 7.22 (2H, m), 5.63 (1H, t), 4.92 (1H, septet), 3.79 (1H, ddd), 3.60 (1H, m), 1.82 (4H, m), 1.60 (6H, d), 1.55 (2H, m).

Provenance & Evidence