3,4,5-Trimethoxyphenol → 5,7-Dimethyl-2-(4-nitrophenyl)-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazine

HRID 1270305Notes

Reaction equation

CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([OH:19])[CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16].[CH3:20][C:21]1[N:22]=[C:23]([CH3:44])[N:24]2[C:29]=1[C:28](N1C=NC=N1)=[N:27][C:26]([C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[N:25]2>O1CCCC1>[CH3:20][C:21]1[N:22]=[C:23]([CH3:44])[N:24]2[C:29]=1[C:28]([O:19][C:11]1[CH:12]=[C:13]([O:17][CH3:18])[C:14]([O:15][CH3:16])=[C:9]([O:8][CH3:7])[CH:10]=1)=[N:27][C:26]([C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=1)=[N:25]2

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 40 mg (0.33 mmol) of potassium tert-butoxide and 60 mg (0.33 mmol) of 3,4,5-trimethoxyphenol in 50 ml of tetrahydrofuran is stirred for 30 min. 70 mg (0.22 mmol) of 5,7-dimethyl-2-(4-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo-[5,1-f][1,2,4]triazine from example 11A are added thereto and the mixture is heated for 3 h at 70° C. After cooling, the solvent is removed and the residue is purified by chromatography (eluent gradient: dichloromethane/methanol 200:1-100:1).

Workup

temperatureAfter cooling
customthe solvent is removed
customthe residue is purified by chromatography (eluent gradient: dichloromethane/methanol 200:1-100:1)

Sources & evidence

ORD record: ord-1715d1056c5c44dbbddb2adc79aaa80b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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