Diethyl Ether → Imidazo[1,2-d][1,2,4]triazin-8(7H)-one

HRID 1723676Notes

Reaction equation

HRID 1723676 reaction equation
[NH:1]([C:3]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)=[O:4])[NH2:2].[CH3:10]OC(OC)N(C)C.C(OCC)C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[N:6]1[CH:7]=[CH:8][N:9]2[C:5]=1[C:3](=[O:4])[NH:1][N:2]=[CH:10]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 78373Dimethylformamide dimethyl acetalHCID 12493320HCID 12493320, compound

Product 1

HCID 45087660Imidazo[1,2-d][1,2,4]triazin-8(7H)-oneYield 20%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
100 °C

Procedure

2-Hydrazinocarbonylimidazole (prepared according to the procedure described in EP-A-0713876) (1.00 g, 7.93 mmol) was suspended in Dowtherm A (6 ml), N,N-dimethylformamide dimethyl acetal (1.89 g, 15.9 mmol) added and the mixture heated at 100° C. for 1.5 h then at 210° C. for 18 h. The mixture was allowed to cool to room temperature, diethyl ether (100 ml) added and the precipitated solid was filtered. The brown solid was purified by dry flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (5-12%). Collecting appropriate fractions gave 7H-imidazo[1,2-d][1,2,4]triazin-8-one (216 mg, 20%) as an off-white solid: δH (400 MHz, CDCl3) 7.59 (1H, d, J 1), 7.91 (1H, d, J 1), 8.74 (1H, s), 12.39 (1H, s).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated solid was filtered
  3. customThe brown solid was purified
  4. dry with materialby dry flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (5-12%)
  5. customCollecting appropriate fractions

Sources & evidence

ORD record
ord-0811cb2b9fbd49c896131525de938986
Source dataset
uspto-grants-2009_02
Patent number
US07485640B2

Reaction notes

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