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

HRID 1297195Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH2:24][O:25][CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:27]([C:31]1[N:32]=[N:33][C:34]([C:37]([O:39][CH3:40])=[O:38])=NN=1)([O:29][CH3:30])=[O:28].N1C=NN=CN=1.CCOC(C)=O.C(Cl)Cl>C1(C)C=C(C)C=C(C)C=1>[CH3:22][O:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:13]([C:12]2[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:31]([C:27]([O:29][CH3:30])=[O:28])[N:32]=[N:33][C:34]=2[C:37]([O:39][CH3:40])=[O:38])=[C:14]([O:23][CH2:24][O:25][CH3:26])[CH:15]=1

Participants

Conditions

Temperature: 140 °C

Procedure

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).

Workup

temperaturewas cooled to 25° C.
customthe solvent was evaporated

Sources & evidence

ORD record: ord-23b4023810de4c25a9607e6c0f8049a9
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250409B2

Reaction notes

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