Ethyl orthoformate → 8-Methyl-6-(3-pyridinyl)imidazo[1,5-d]-1,2,4-triazin-1(2H)-one

HRID 1252370Notes

Reaction equation

HRID 1252370 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:13]([NH:15][NH2:16])=[O:14].[CH2:17](OC(OCC)OCC)C>C(O)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:4]2[C:3]=1[C:13](=[O:14])[NH:15][N:16]=[CH:17]2

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 68635306HCID 68635306, compound

Product 1

HCID 201398908-Methyl-6-(3-pyridinyl)imidazo[1,5-d]-1,2,4-triazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
220 °C

Procedure

A 5 g portion of 5-methyl-2-(3-pyridinyl)-1H-imidazole-4-carboxylic acid, hydrazide in 100 ml of triethoxymethane was stirred at reflux for 18 hours in an oil bath at 220° C. The volatiles were boiled off as the temperature of the oil bath rose to 250°-260° C. The residue in the flask melted, then solidified, was kept at 250°-260° C. for 30 minutes and then cooled to room temperature. The solid was boiled in 200 ml of ethanol, the solid collected, dissolved in 100 ml of boiling methyl cellosolve, treated with charcoal and clarified. The filtrate was cooled at -5° C., the solid collected washed with ethanol and dried, giving 600 mg of the desired product, mp 292°-295° C. (dec.).

Workup

  1. customrose to 250°-260° C
  2. temperaturecooled to room temperature
  3. customthe solid collected
  4. dissolutiondissolved in 100 ml of boiling methyl cellosolve
  5. additiontreated with charcoal
  6. temperatureThe filtrate was cooled at -5° C.
  7. customthe solid collected
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-20ee0da76d5c4323b754b25808a508c7
Source dataset
uspto-grants-1988_05
Patent number
US04743586

Reaction notes

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