Cyanoacetamide → 4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 577442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577442
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C(O[K])(C)(C)C.[Si:13]([O:20][CH2:21][C:22]#[C:23][C:24](=O)[CH3:25])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CS(C)=O>[Si:13]([O:20][CH2:21][C:22]1[CH:23]=[C:24]([CH3:25])[NH:6][C:4](=[O:5])[C:3]=1[C:1]#[N:2])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 7898CyanoacetamideHCID 12764994HCID 12764994, VerbindungHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 682948094-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of 2-cyanoacetamide (1.74 g, 20.7 mmol) and tBuOK (2.32 g, 20.7 mmol) in DMSO (48 mL) was added 5-{[tert-butyl(dimethyl)silyl]oxy}pent-3-yn-2-one (Cpd G, 4.4 g, 21.0 mmol) dropwise. The reaction mixture turned bright orange. The reaction mixture was stirred for 2 hours at 0° C., then quenched with NH4Cl (sat., aq.) and diluted with water causing solids to precipitate out. The solids were collected via filtration and dried under vacuum to give 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cpd H, 5.0 g, 86%) as a tan solid.

Aufarbeitung

  1. customquenched with NH4Cl (sat., aq.)
  2. additiondiluted with water causing solids
  3. customto precipitate out
  4. filtrationThe solids were collected via filtration
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8edd1469bcfb4be1b0f7980c8d1e45c2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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