1,2-Dichloroethane → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

1,2-Dichloroethane (0.25 mL) was added to a mixture of methyl 5-azido-2,6-bis(4-methoxyphenyl)pyrimidine-4-carboxylate (154 mg, 0.393 mmol), rhodium octanoate dimer (31 mg, 0.039 mmol) and crushed 4 A° molecular sieves (154 mg) in a microwave vial. The vial was sealed and heated at 60° C. overnight. This was diluted with mixture of dichloromethane and EtOAc (9:1), filtered, and the solvent removed from the filtrate. Radial silica chromatography (step gradient elution with methylene chloride containing 0 to 5% EtOAc) afforded methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylate (100 mg) as a yellow solid. MS (ESI) m/z 364.0 (M+H). 1H NMR (DMSO-d6) δ ppm 11.68 (1H, s), 8.48 (2H, d, J=8.85 Hz), 8.23 (1H, d, J=8.85 Hz), 7.24 (1H, d, J=2.14 Hz), 7.11 (2H, d, J=8.85 Hz), 6.99 (1H, dd, J=8.85, 2.14 Hz), 4.09 (3H, s), 3.93 (3H, s), 3.86 (3H, s).

Provenance & Evidence