Dimethylformamide → (3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

HRID 426175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426175
[CH3:1][O:2][CH:3]([O:27][CH3:28])[C:4]1[CH:5]=[C:6]([CH:11]([C:14]2[C:19]([CH:20]([CH3:22])[CH3:21])=[C:18]([O:23][CH3:24])[N:17]=[C:16]([O:25][CH3:26])[N:15]=2)C#N)[CH:7]=[C:8]([CH3:10])[CH:9]=1.[H-].[Na+].CN(C=[O:35])C>>[CH3:1][O:2][CH:3]([O:27][CH3:28])[C:4]1[CH:5]=[C:6]([C:11]([C:14]2[C:19]([CH:20]([CH3:22])[CH3:21])=[C:18]([O:23][CH3:24])[N:17]=[C:16]([O:25][CH3:26])[N:15]=2)=[O:35])[CH:7]=[C:8]([CH3:10])[CH:9]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59184766(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

Produkt 1

HCID 59184803(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanoneAusbeute 98 %

Versuchsvorschrift

To a stirred solution of (3-dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (3.4 g, 8.8 mmol) in anhydrous DMF (36 ml) at room temperature under nitrogen atmosphere, was added 60% sodium hydride (0.423 g, 10.6 mmol). After 20 min., oxygen was bubbled into the mixture for 3 hr. The mixture was then partitioned between ether and water, The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 3.26 g (98%) of a pale yellow solid. m.p. 86-88° C.; 1H NMR (300 MHz, CDCl3) δ 1.22 (6H, d, J=6.3 Hz), 2.41 (3H, s), 2.81 (1H, m), 3.31 (6H, s), 3.93 (3H, s), 4.06 (3H, s), 5.36 (1H, s), 7.53 (1H, s), 7.64 (1H, s), 7.71 (1H, s).

Aufarbeitung

  1. customoxygen was bubbled into the mixture for 3 hr
  2. customThe mixture was then partitioned between ether and water
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-7fe29f77de364449ad613905361a3345
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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