Potassium Carbonate → HCID 67297667, compound

HRID 215911Notes

Reaction equation

HRID 215911 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8](Br)([CH3:10])[CH3:9].[Cl:14][C:15]1[C:20]([OH:21])=[CH:19][C:18]([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:17]([F:35])[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8]([O:21][C:20]1[CH:19]=[C:18]([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:17]([F:35])=[CH:16][C:15]=1[Cl:14])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 86657470HCID 86657470, compound

Product 1

HCID 67297667HCID 67297667, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Bromo-2-methylpropionylamino)propionic acid methyl ester (224 mg) and 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (250 mg) were dissolved in acetonitrile 5 ml. After addition of K2CO3 (204 mg), the reaction mixture was heated for 12 hours under reflux, cooled and diluted with ethyl acetate (50 mL). After washing with water (50 mL), thus obtained organic layer was dried with magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography to give the target compound (240 mg).

Workup

  1. temperaturethe reaction mixture was heated for 12 hours
  2. temperatureunder reflux
  3. temperaturecooled
  4. washAfter washing with water (50 mL), thus obtained organic layer
  5. dry with materialwas dried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c39341c7b547405882c8e9ed63cbe419
Source dataset
uspto-grants-2012_06
Patent number
US08193198B2

Reaction notes

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