Potassium Carbonate → 5,7-dimethyl-2-(3-nitrophenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-4-amine

HRID 1270308Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([CH3:25])[N:5]2[C:10]=1[C:9]([N:11]1[CH:15]=NC=N1)=[N:8][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)=[N:6]2.[CH3:26][O:27][C:28]1[CH:29]=C([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])N.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]([CH3:25])[N:5]2[C:10]=1[C:9]([NH:11][C:15]1[CH:29]=[C:28]([O:27][CH3:26])[C:34]([O:35][CH3:36])=[C:33]([O:37][CH3:38])[CH:32]=1)=[N:8][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)=[N:6]2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 350 mg (1.04 mmol) of 5,7-dimethyl-2-(3-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine from example 12A in DMF is treated with 290 mg (1.56 mmol) of 3,4,5-trimethoxyaniline and 220 mg (1.56 mmol) of potassium carbonate. The reaction mixture is stirred overnight at 90° C. After cooling, the solvent is removed on a rotary evaporator, the residue is treated twice more with toluene and the solvent is removed in vacuo. The product is extracted by stirring with a little methanol and filtered off with suction.

Workup

temperatureAfter cooling
customthe solvent is removed on a rotary evaporator
additionthe residue is treated twice more with toluene
customthe solvent is removed in vacuo
extractionThe product is extracted
stirringby stirring with a little methanol
filtrationfiltered off with suction

Sources & evidence

ORD record: ord-e36e29783b3944eea0dc0bc48dd212f7
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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