Uracil → HCID 86723841, compound

HRID 576742Notes

Reaction equation

HRID 576742 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].CN(CCN(C)C)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>CO.CN(C)C=O.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[C:23]([N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 1174UracilHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 86723841HCID 86723841, compoundYield 4.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 86634112HCID 86634112, compoundSolvent

Procedure

To a solution of uracil (8.9 g), copper(II) acetate (9.6 g), N,N,N,N-tetramethylethylenediamine (10.2 ml) in methanol/dimethy formamide/water (500/100/100 ml) was added 3-trifluoromethylphenyl boronic acid (10.0 g) and the resulting mixture was stirred at room temperature for twelve hours. The reaction mixture was concentrated under reduced pressure so as to remove methanol and thereto was added water (100 ml). The resulting mixture was extracted with ethyl acetate (100 ml×3) and the organic layer was washed with water (100 ml×2) and saturated saline (50 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (650.0 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure so as
  2. customto remove methanol
  3. additionwas added water (100 ml)
  4. extractionThe resulting mixture was extracted with ethyl acetate (100 ml×3)
  5. washthe organic layer was washed with water (100 ml×2) and saturated saline (50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-004422eaae934a5581d4b278f35941d4
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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