Pyridine → Pyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione

HRID 493129Notes

Reaction equation

HRID 493129 reaction equation
Cl[C:2](OCC)=[O:3].[NH2:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([NH2:15])=[O:14].N1C=CC=CC=1>O1CCOCC1>[NH:7]1[C:2](=[O:3])[NH:15][C:13](=[O:14])[C:9]2=[CH:10][CH:11]=[CH:12][N:8]12

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 15604988Pyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dioneYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
155 °C

Procedure

Ethyl chloroformate (4.9 ml, 51 mmole) was added dropwise to a stirred mixture of 1-amino-1H-pyrrole-2-carboxamide (5.85 gm, 46.7 mmole, Journal of Heterocyclic Chemistry, 1994, 31, 781) and dry pyridine (4.2 mL, 51 mmole) in dry dioxane (48 mL) under N2 at RT. This was heated at reflux for 1 hr and then the solvent was removed. The residue was heated at 155° C. for 17 hr and then allowed to cool to RT. This was triturated with methanol and the solid was collected by filtration and washed with cold methanol to give the product, 4.43 gm (63% yield): MS: 152 (M+H)+; HPLC Ret Time: 0.36 min (YMC Xterra S7 3.0×50 mm column, 2 min gradient, 5 mL/min).

Workup

  1. temperatureThis was heated
  2. temperatureat reflux for 1 hr
  3. customthe solvent was removed
  4. temperatureto cool to RT
  5. customThis was triturated with methanol
  6. filtrationthe solid was collected by filtration
  7. washwashed with cold methanol
  8. customto give the product, 4.43 gm (63% yield)
  9. custom0.36 min (YMC Xterra S7 3.0×50 mm column, 2 min gradient, 5 mL/min)

Sources & evidence

ORD record
ord-7346175421b544849ea8be03f9242cb0
Source dataset
uspto-grants-2009_05
Patent number
US07534792B2

Reaction notes

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