2-Hydrazinopyrazine → methyl[3-methyl-5-phenyl-1-(pyrazin-2-yl)-1H-pyrazol-4-yl]acetate

HRID 2068478Notes

Reaction equation

[NH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][N:8]=1)[NH2:2].O=[C:10]([CH3:25])[CH:11]([C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14]>C(O)C>[CH3:16][O:15][C:13](=[O:14])[CH2:12][C:11]1[C:10]([CH3:25])=[N:2][N:1]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][N:8]=2)[C:17]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 135 °C

Procedure

0.378 g (3.330 mmol) of 3-hydrazinopyrazine in 12.5 ml of ethanol was added to 0.600 g (2.561 mmol) of methyl 4-oxo-3-(phenylcarbonyl)pentanoate, and the mixture was heated at 135° C. in a sealed vessel in a microwave oven for 1.5 h. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane and washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.115 g (13.8% of theory) of a light-yellow wax.

Workup

customThe solvent was removed under reduced pressure
washwashed twice with in each case 25 ml of water
dry with materialThe combined organic phases were dried over sodium sulfate
customthe solvent was removed under reduced pressure
customChromatography of the residue gave 0.115 g (13.8% of theory) of a light-yellow wax

Sources & evidence

ORD record: ord-c65a45ca98364aad901fab237359ab2e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08298994B2

Reaction notes

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