Potassium Carbonate → HCID 86670149, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL vial were added 4-bromo-2-((2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)benzonitrile (105 mg, 0.250 mmol), potassium carbonate (69.0 mg, 0.499 mmol), PdCl2(dppf) (18.26 mg, 0.025 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.042 mL, 0.300 mmol) in dioxane (2 mL) and water (0.4 mL). The resulting brown suspension was stirred overnight at 100° C. The reaction mixture was subsequently diluted with EtOAc and washed with saturated NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography (SiO2, 4 g column, 2:8 to 8:2 EtOAc/Hexane gradient) to give the title compound as a tan solid (52 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (s, 3H), 2.92-3.08 (m, 3H), 3.10-3.20 (m, 2H), 3.24-3.32 (m, 2H), 3.40-3.52 (m, 2H), 3.62-3.75 (m, 2H), 3.81-3.90 (m, 2H), 3.91-4.00 (m, 2H), 4.21-4.31 (m, 2H), 4.41-4.63 (m, 3H), 7.30-7.38 (m, 2H), 7.38-7.55 (m, 3H), 7.67-7.73 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C18H18ClN5O, 356.1. found 356.1.

Provenance & Evidence