Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate → 3-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone

HRID 398388Notes

Reaction equation

[CH2:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].Br[C:11]1[C:12](=[O:24])[N:13]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([CH3:17])=[CH:15][N:16]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH2:1]([C:3]1[C:8]([NH:9][C:11]2[C:12](=[O:24])[N:13]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([CH3:17])=[CH:15][N:16]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-ethyl-3-aminopyridine (0.35 g, 2.8 mMol, 2 eq) from step 2 above and 3-bromo-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone (0.39 g, 1.4 mMol) in 1 mL of nitrobenzene was heated at 200 ° C. for 2 h. The reaction was concentrated in vacuo and the residue purified by flash silica gel chromatography using 1% methanol in methylene chloride as an eluent to afford the title compound as a yellow oil that crystallizes upon sitting. (0.058 g; HPLC RT=4.45 min, method A).

Workup

concentrationThe reaction was concentrated in vacuo
customthe residue purified by flash silica gel chromatography

Sources & evidence

ORD record: ord-23a1c050591b4dd991041f4cac13ed91
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610692B1

Reaction notes

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