Ammonium Hydroxide → 4,6-Bis(1,1-dimethylethyl)-5-hydroxy 2-methylpyrimidine

HRID 6341

Reaktionsgleichung

Reaktionsgleichung von HRID 6341
[CH3:1][C:2]([C:5]1[N:6]=[C:7]([CH3:16])[O:8][C:9]=1[C:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:4])[CH3:3].[OH-].[NH4+:18]>>[CH3:1][C:2]([C:5]1[C:9]([OH:8])=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:18]=[C:7]([CH3:16])[N:6]=1)([CH3:4])[CH3:3]

Komponenten

3

Edukt 2

HCID 14923Ammonium HydroxideHCID 189253781-[4-(1,1-Dimethylethyl)-2-methyl-5-oxazolyl]-2,2-dimethyl-1-propanone

Produkt 1

HCID 98778664,6-Bis(1,1-dimethylethyl)-5-hydroxy 2-methylpyrimidineAusbeute 75 %

Versuchsvorschrift

A mixture of 1-[4-(1,1-dimethylethyl)-2 methyl-5-oxazolyl]-2,2-dimethyl-1 propanone (8.5 g, 38 mmol) and concentrated ammonium hydroxide (100 mL) is heated at 180° C. for 36 hours in a steel bomb. The reaction mixture is cooled and the excess ammonia is evaporated on the rotovap. The pH of the resulting mixture is adjusted to pH 6 with concentrated HCl with ice bath cooling. The product is extracted into ether (3×250 mL) and the organic layer is dried (MgSO4) and evaporated. The residue is purified by flash chromatography (silica, 7% EtOAc/hexane) to give pure 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-methylpyrimidine (6.35 g, 75%) as a partial hydrate; mp 62°-65° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customthe excess ammonia is evaporated on the rotovap
  3. customThe pH of the resulting mixture is adjusted to pH 6 with concentrated HCl with ice bath
  4. temperaturecooling
  5. extractionThe product is extracted into ether (3×250 mL)
  6. dry with materialthe organic layer is dried (MgSO4)
  7. customevaporated
  8. customThe residue is purified by flash chromatography (silica, 7% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c60e5ad8c697434fa67dd662437ae58d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248682

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