Sodium Bicarbonate → N-(5-(4-(cyclohexylthio)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzenesulfon-amide

Participants

Reaction Steps

A mixture of 6-chloro-4-(cyclohexylthio)pyrido[3,2-d]pyrimidine (Intermediate 15) (0.12 g, 0.429 mmol), N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (Intermediate 2) (0.12 g, 0.429 mmol), 1 N aq. sodium bicarbonate (0.858 ml, 0.858 mmol) and PdCl2(dppf)-CH2Cl2 (0.035 g, 0.043 mmol) in dioxane (2.14 ml) was subjected to microwave irradiation for 1 hour at 110° C., and cooled to room temperature. The reaction mixture was filtered through a Celite pad and washed with DCM. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to give N-(5-(4-(cyclohexylthio)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzenesulfon-amide (0.09 g, 89%) as a brown solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.26-1.28 (1H, m), 1.34-1.43 (1H, m), 1.52-1.85 (4H, m), 1.85-1.87 (2H, m), 2.19-2.23 (2H, m), 4.12-4.19 (1H, m), 7.48-7.58 (3H, m), 7.92 (2H, d, J=8.8 Hz), 8.21 (1H, d, J=8.8 Hz), 8.32 (1H, d, J=9.2 Hz), 8.41-8.43 (2H, m), 8.99 (1H, s), 9.13 (1H, s). m/z=478.1 [M+1]+.

Provenance & Evidence