Sodium hydride → (3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

HRID 426132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426132
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][C:24]#[N:25])[CH:19]=[C:20]([Cl:22])[CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]([C:2]2[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=2)[C:24]#[N:25])[CH:19]=[C:20]([Cl:22])[CH:21]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 126899782-(3,5-Dichlorophenyl)acetonitrileHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidine

Produkt 1

HCID 59184725(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrileAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (9.8 g, 45 mmol) and (3,5-Dichloro-phenyl)-acetonitrile (8.0 g, 43 mmol) in anhydrous DMF (70 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (3.44 g, 86 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ethyl acetate and purified by silica gel column chromatography (eluent, EA:hexanes (1:9)) to afford 9.6 g (61%) of the title compound as a white solid. m.p. 135-136° C.; 1H NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=7.0 Hz), 1.18 (3H, d, J=7.0 Hz), 2.97 (1H, m), 3.99 (6H, s), 5.33 (1H, s), 7.25-7.33 (3H, m).

Aufarbeitung

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ethyl acetate
  3. custompurified by silica gel column chromatography (eluent, EA:hexanes (1:9))

Quellen und Nachweise

ORD-Eintrag
ord-c8d0c89303dd4a0883ba1478c8d06eeb
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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