2,3-Diaminobut-2-enedinitrile → 5-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile

HRID 915021Notes

Reaction equation

[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11](=O)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[N:5]1)([CH3:3])[CH3:2].[NH2:21][C:22](=[C:25]([NH2:28])[C:26]#[N:27])[C:23]#[N:24]>C(#N)C>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:21]=[C:22]([C:23]#[N:24])[C:25]([C:26]#[N:27])=[N:28][C:12]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 72.5 °C

Procedure

A mixture of 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione (1.15 g) and 2,3-diamino-2-butenedinitrile (0.46 g) in acetonitrile (6 ml) was heated at 70-75° C. for 3 hours. A reaction mixture was concentrated under reduced pressure and subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile as a solid (1.30 g).

Workup

concentrationA reaction mixture was concentrated under reduced pressure
additionsubjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v)

Sources & evidence

ORD record: ord-34f7683132c5432ba17161c0b1522536
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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