2-Amino-2,3-dimethylbutanamide → 2-Methyl-4-(4-methyl-4-isopropylimidazolin-5-on-2-yl)-pyrimidine-5carboxylic acid

HRID 5328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5328
[CH3:1][C:2]1[N:7]=[C:6]([C:8](OCC)=O)[C:5]([C:13]([O:15]CC)=[O:14])=[CH:4][N:3]=1.[NH2:18][C:19]([CH3:26])([CH:23]([CH3:25])[CH3:24])[C:20]([NH2:22])=[O:21]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[NH:22][C:20](=[O:21])[C:19]([CH3:26])([CH:23]([CH3:25])[CH3:24])[N:18]=2)[C:5]([C:13]([OH:15])=[O:14])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 12312061HCID 12312061, Verbindung

Produkt 1

HCID 197955792-Methyl-4-(4-methyl-4-isopropylimidazolin-5-on-2-yl)-pyrimidine-5carboxylic acidAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 98.8 g (0.415 mole) of diethyl 2-methylpyrimidine-4,5-dicarboxylate (compare, for example, J. Heterocycl. Chem. 2, 202-204 [1965]) and 54.0 g (0.415 mole) of 2-amino-2,3-dimethylbutyramide in 700 ml of anhydrous toluene there are added in portions 102.2 g (0.913 mole) of potassium tert.-butylate, and the mixture is subsequently stirred for 16 hours at 80° C. For working-up, the reaction mixture is cooled, the solid which has precipitated is filtered, washed several times with diethyl ether and subsequently dissolved in water. The aqueous solution is brought to pH 5 using half-concentrated hydrochloric acid, and the mixture is extracted five times using 200 ml portions of dichloromethane. The combined organic extracts are dried over sodium sulphate and concentrated in vacuo. The residue can be purified by chromatography on silica gel. 59 g (51% of theory) of 2-methyl-4-(4-methyl-4-isopropylimidazolin-5-on-2-yl)-pyrimidine-5carboxylic acid of melting point 56°-57° C. are obtained.

Aufarbeitung

  1. temperaturethe reaction mixture is cooled
  2. customthe solid which has precipitated
  3. filtrationis filtered
  4. washwashed several times with diethyl ether
  5. dissolutionsubsequently dissolved in water
  6. extractionthe mixture is extracted five times
  7. dry with materialThe combined organic extracts are dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue can be purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-05aff642a9524aeeb782b83184544cc8
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244865

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