Potassium Carbonate → HCID 18619280, compound

HRID 1862280Notes

Reaction equation

HRID 1862280 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:20][C:19]=1[OH:38].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:33])([F:35])[F:34])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:20][C:19]=1[O:38][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 18619157HCID 18619157, compound

Product 1

HCID 18619280HCID 18619280, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g of 6-chloro-2-(methoxycarbonyl)methoxy-3-nitropyridine, 1.37 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol, 0.67 g of potassium carbonate and 5 ml of N,N-dimethylformamide was stirred for 1 hour at room temperature, then at 50° C. for 30 minutes. The resulted residue was added to ice water, extracted with ethyl acetate, and organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.25 g of 6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxy-3-nitropyridine.

Workup

  1. waitat 50° C. for 30 minutes
  2. extractionextracted with ethyl acetate, and organic layer
  3. washwas washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f159b88a5644baf8efab2cd371aca65
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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