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Sodium hydride → (5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone

HRID 426185
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 426185
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:15]([C:18]2[C:23]([CH2:24][CH3:25])=[C:22]([O:26][CH3:27])[N:21]=[C:20]([O:28][CH3:29])[N:19]=2)C#N)[CH:11]=[C:12]([CH3:14])[CH:13]=1)(C)(C)C.[H-].[Na+].O.C1(C)C=CC(S(O)(=O)=[O:42])=CC=1>CN(C=O)C.CO>[CH2:24]([C:23]1[C:18]([C:15]([C:10]2[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH2:7][OH:6])[CH:9]=2)=[O:42])=[N:19][C:20]([O:28][CH3:29])=[N:21][C:22]=1[O:26][CH3:27])[CH3:25]
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Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178437280HCID 178437280, Verbindung

Produkt 1

HCID 59184675(5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanoneAusbeute 628,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-phenyl]-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (3.74 g, 8.47 mmol) in anhydrous DMF (40 ml), was added 60% sodium hydride (373 mg, 9.32 mmol). After 20 min., oxygen was bubbled into the reaction mixture for 3 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was stirred with p-toluenesulfonic acid monohydrate (152 mg, 0.8 mmol) in methanol (10 ml) for 2 hr. at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2)) to afford 1.59 g (59%) of a white solid. m.p. 101-103° C.; 1H NMR (200 MHz, CDCl3) δ 1.05 (3H, t, J=7.4 Hz), 2.35-2.48 (5H, m), 3.93 (3H, s), 4.06 (3H, s), 4.63 (2H, br. S), 7.40 (1H, s), 7.56 (1H, s), 7.60 (1H, s).

Aufarbeitung

  1. customoxygen was bubbled into the reaction mixture for 3 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customat room temperature
  8. customThe mixture was evaporated in vacuo
  9. customthe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2))

Quellen und Nachweise

ORD-Eintrag
ord-f665b91ca31842808c998b0bf45f5ae2
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106064B2

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