Diisopropylethylamine → 5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile

HRID 576806

Reaktionsgleichung

Reaktionsgleichung von HRID 576806
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([C:10]2[N:14](C3C=CC(C#N)=CC=3)[N:13]=[CH:12][C:11]=2I)=[C:6]([CH3:24])[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:4]1=[O:35])C.C([N:39]([CH2:43][CH3:44])C(C)C)(C)C.[CH3:45][S-:46].[Na+]>CN(C)C=O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][N:3]1[C:8](=[O:9])[C:7]([C:10]2[C:11]([S:46][CH3:45])=[CH:12][N:13]([C:6]3[CH:7]=[CH:10][CH:11]=[C:44]([CH:24]=3)[C:43]#[N:39])[N:14]=2)=[C:6]([CH3:24])[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=2)[C:4]1=[O:35]

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 86723911HCID 86723911, Verbindung

Produkt 1

HCID 867239105-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 4-(5-(3-ethyl-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-4-iodo-1H-pyrazol-1-yl)benzonitrile (prepared in Example 268) (98.1 mg) in N,N-dimethy formamide (1.0 ml) were added palladium dibenzylidene acetone complex (15.9 mg), 1,1′-bis(diphenylphosphino)ferrocene) (18.9 mg), N,N-diisopropylethylamine (33.8 μl) and sodium methanethiolate (13.4 mg) and the resulting mixture was stirred at 110° C. for four hours. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with saturated saline (20 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 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile (57.4 mg).

Aufarbeitung

  1. washwashed with saturated saline (20 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b496b463bad3458ea4b2e23b82d8ca29
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040516B2

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