Potassium Carbonate → HCID 18519614, compound

HRID 1368022Notes

Reaction equation

HRID 1368022 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]1=[O:23].Br[CH:25]([CH3:31])[C:26](OCC)=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:9][C:6]1[C:7]2[O:8][CH:25]([CH3:31])[C:26](=[O:27])[NH:1][C:2]=2[C:3]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:10])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 18519614HCID 18519614, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluromethyl-2,4(1H,3H)-pyrimidinedione (1.07 g), ethyl bromopropionate (0.61 g) and potassium carbonate (0.414 g) in acetonitrile (30 ml) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and evaporated to give an amorphous (0.95 g). The amorphous was purified on a silica gel column, eluted with methylene chloride-ethyl acetate (19:1 and 9:1) to give the title compound (0.86 g) as white crystals.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customto give an amorphous (0.95 g)
  5. customThe amorphous was purified on a silica gel column
  6. washeluted with methylene chloride-ethyl acetate (19:1 and 9:1)

Sources & evidence

ORD record
ord-714be82ac16d452095ea82cb6f079091
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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