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

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.09 g, 3.75 mmol), (5-methyl-1H-indazol-4-yl)boronic acid (600 mg, 3.41 mmol), Pd(PPh3)4 (197 mg, 0.170 mmol), and Na2CO3 (2 M, 5.97 mL, 11.9 mmol) in DME (11 mL) was heated in a microwave reactor at 140° C. for 1.5 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (20-100% EtOAc/heptane) to provide 6-benzyl-4-methoxy-2-(5-methyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 386.2 (M+H)+.

Provenance & Evidence