Water → HCID 57714112, Verbindung

HRID 1984257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984257
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1.[CH:23]([CH:25]=[CH2:26])=[O:24].C(N(CC)CC)C.O>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:26]=[CH:25]/[CH:23]=[O:24])=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7847AcroleinHCID 8471TriethylamineHCID 44450361HCID 44450361, Verbindung

Produkt 1

HCID 57714112HCID 57714112, VerbindungAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-[(2,2-Dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile (1.3 g, 2.5 mmoles), acrolein (0.5 ml, 7.4 mmoles), and triethylamine (0.4 ml, 3.1 mmoles) are dissolved in 25 ml of acetonitrile and Pd(OAc)2 (27 mg, 0.12 mmoles) is added at rt. The mixture is stirred at 80° C. for 18 h. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesum sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 423 mg of desired 4-{(2,2-dimethyl-propyl)-[4-((E)-3-oxo-propenyl)-benzyl]-amino}-pyrimidine-2-carbonitrile in 39% yield.

Aufarbeitung

  1. extractionthe organic layer is extracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over magnesum sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ac71930e89a471c986bb77e0af8785f
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544688B2

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