Potassium Carbonate → HCID 18619200, compound

HRID 1862287Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([OH:14])=[CH:4][CH:3]=1.F[C:16]1[CH:21]=[C:20]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])[C:19]([F:35])=[CH:18][C:17]=1[N+:36]([O-:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:35][C:19]1[C:20]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:21][C:16]([O:14][C:5]2[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:17]([N+:36]([O-:38])=[O:37])[CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 6-chloro-3-hydroxy-2-(methoxycarbonyl)methoxypyridine, 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene and N,N-dimethylformamide is added potassium carbonate, and the mixture is stirred for 2 hours at 70° C. The reaction solution is cooled to room temperature, then, poured into ice water, and extracted with ethyl acetate. The organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-6-chloro-2-(methoxycarbonyl)methoxypyridine.

Workup

temperatureThe reaction solution is cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer is washed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-280a8d930fb3430b9b0ec72ee2bdccd1
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06537948B1

Reaction notes

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