Water → 5-(3,3-diethoxyprop-1-ynyl)-3,6-dimethyl-1-(3-trifluoromethylphenyl)-pyrimidin-2,4(1H,3H)-dione

HRID 576738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576738
I[C:2]1[C:3](=[O:21])[N:4]([CH3:20])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].[CH2:22]([O:24][CH:25]([O:28][CH2:29][CH3:30])[C:26]#[CH:27])[CH3:23].C(N(CC)CC)C.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[CH2:22]([O:24][CH:25]([O:28][CH2:29][CH3:30])[C:26]#[C:27][C:2]1[C:3](=[O:21])[N:4]([CH3:20])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8])[CH3:23]

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 662853,3-DiethoxypropyneHCID 867238385-iodo-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione

Produkt 1

HCID 867238635-(3,3-diethoxyprop-1-ynyl)-3,6-dimethyl-1-(3-trifluoromethylphenyl)-pyrimidin-2,4(1H,3H)-dioneAusbeute 1.079,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-iodo-3,6-dimethyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 60) (20.0 mg), propargylaldehyde diethyl acetal (62.5 mg), tetrakis(triphenylphosphine)palladium (5.6 mg), copper iodide (1.0 mg) and triethylamine (68 μL) in tetrahydrofuran (1.0 ml) was stirred at room temperature under nitrogen atmosphere for twelve hours. To the reaction mixture was added water (10 ml) and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 5-(3,3-diethoxyprop-1-ynyl)-3,6-dimethyl-1-(3-trifluoromethylphenyl)-pyrimidin-2,4(1H,3H)-dione (216.0 mg).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate (10 ml×2)
  2. washThe organic layer was washed with saturated saline (20 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a3fec0ec3b194e9ab00b7b84134ccc76
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040516B2

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