Pyridinium chloride → 1-(5-Hydroxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dione

HRID 1179678Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]2=[O:18])=[N:7][CH:8]=1.Cl.N1C=CC=CC=1>ClCCl>[OH:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[C:10](=[O:18])[CH2:11][C:12]([CH3:16])([CH3:17])[CH2:13][C:14]2=[O:15])=[N:7][CH:8]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 1-(5-methoxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dione (0.99 g, 3.97 mmol) and pyridine hydrochloride (1.50 g, 7.99 mmol) was heated at 190° C. for 2.5 hours. After cooling to room temperature the reaction mixture was dissolved in a small amount of dichloromethane and filtered over a short pad of silicagel and washed with ethyl acetate. Evaporation of the solvent in vacuo yielded the title compound (0.60 g, 64% yield) as a white solid.

Workup

temperatureAfter cooling to room temperature the reaction mixture
filtrationfiltered over a short pad of silicagel
washwashed with ethyl acetate
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-215713d91ce5401780077bb76ea36a94
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279470B2

Reaction notes

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