Sodium Carbonate → 6-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.0 g, 3.45 mmol) in DME (10.0 mL) in a 20 mL microwave reaction vial was added 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole (1.57 g, 3.80 mmol). Then 2 M aqueous Na2CO3 (5.6 mL, 11.22 mmol) was added. The reaction mixture was degassed via a series of 3 argon/vacuum cycles and then placed under an atmosphere of argon. Then Pd(Ph3P)4 (0.399 g, 0.345 mmol) was added and the vial was sealed and heated via microwave irradiation at 140° C. for 90 minutes. The reaction mixture was cooled to room temperature and diluted with Et2O and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (27-48% ethyl acetate/heptanes) to provide 6-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine as a white solid. MS (ESI+) m/z 539.3 (M+H)+.

Provenance & Evidence