Water → HCID 44450361, Verbindung

HRID 1163024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163024
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C-]#N.[Na+].[N:25]12CCN(CC1)C[CH2:26]2.O>CS(C)=O>[CH3:19][C:18]([CH3:21])([CH3:20])[CH2:17][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:26]#[N:25])[N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8929Sodium CyanideHCID 9237DabcoHCID 57714136HCID 57714136, Verbindung

Produkt 1

HCID 44450361HCID 44450361, VerbindungAusbeute 861,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

(2-Chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-(4-iodo-benzyl)-amine (10.0 g, 24.0 mmoles) and sodium cyanide (5.6 g, 0.12 moles) are dissolved in 40 ml of DMSO and 1,4-diaza bicyclo[2,2,2]octane (0.27 g, 2.4 mmoles) is added at rt. The mixture is stirred at 75° C. for 21 h. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 8.4 g of desired 4-[(2,2-dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile in 86% yield.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0f5cc0aa302b40e18fb59753a183ab10
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820818B2

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