Potassium Carbonate → HCID 18619268, compound

HRID 1862257Notes

Reaction equation

[OH:1][C:2]1[C:3]([O:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH3:11])=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.F[C:17]1[CH:22]=[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])[C:20]([F:36])=[CH:19][C:18]=1[N+:37]([O-:39])=[O:38].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:36][C:20]1[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])=[CH:22][C:17]([O:1][C:2]2[C:3]([O:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH3:11])=[N:4][C:5]([CH3:8])=[N:6][CH:7]=2)=[C:18]([N+:37]([O-:39])=[O:38])[CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 5-hydroxy-4-{1-(methoxycarbonyl)ethoxy}-2-methylpyrimidine, 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 1 hour 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 5-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-{1-(methoxycarbonyl)ethoxy}-2-methylpyrimidine.

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-d95de4bebfca4f0f9a3d3c859644adfe
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06537948B1

Reaction notes

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