1,3-Dioxane-4,6-dione, 5-[[(6-methoxy-3-pyridinyl)amino]methylene]-2,2-dimethyl- → 6-methoxy-1,5-naphthyridin-4-ol

HRID 1042776Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][CH:10]=[C:11]2[C:16](=[O:17])OC(C)(C)OC2=O)=[CH:5][CH:4]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:10]=[CH:11][C:16]2=[O:17]

Participants

Conditions

Temperature: 250 °C

Procedure

A suspension of 5-((6-methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (51.3 g, 0.185 mol) in diphenylether (1275 mL) was heated to 250° C. under nitrogen atmosphere for 20 min. The reaction mixture was cooled to RT and diluted with hexane. The gummy solid was then triturated with hexane to obtain 6-methoxy-1,5-naphthyridin-4(1H)-one as a pale brown color solid.

Workup

temperatureThe reaction mixture was cooled to RT
customThe gummy solid was then triturated with hexane

Sources & evidence

ORD record: ord-405b923aa1cc4732abf67bfa1c661d57
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557816B2

Reaction notes

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