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

HRID 2384527Notes

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

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

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

Sources & evidence

ORD record: ord-a7ef9e29da9a40fa9cd9803d5e640b21
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263765B2

Reaction notes

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