1,2,4,5-Tetrazine → Dimethyl 4-(4,5-Dimethoxy-2-(methoxymethoxy)phenyl)-5-(3,4-dimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 6 (1.10 g, 3.07 mmol, 1.0 equiv) and 3,6-dicarbomethoxy-1,2,4,5-tetrazine (2,13 0.91 g, 4.60 mmol, 1.5 equiv) in mesitylene (15.4 mL) was warmed at 140° C. under Ar for 24 h. Additional 2 (0.91 g, 4.60 mmol, 1.5 equiv) was added, and the mixture was maintained at 140° C. for an additional 24 h before the reaction mixture was cooled to 25° C. and the solvent was evaporated. Chromatography (SiO2, 4.5 (20 cm, 30% EtOAc/CH2Cl2) provided 7 (1.49 g, 92% yield) as an orange oil. An analytically pure sample was prepared by recrystallization from EtOAc-hexanes: mp 131-133° C.; FABHRMS (NBA/NaI) m/z 551.1663 (M+Na+, C26H28N2O10 requires 551.1642).

Provenance & Evidence