Methyl p-tolylacetate → 5-(4-Methyl-benzyl)-3-(1-methyl-4-phenyl-butyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrirnidin-7-one

HRID 989732

Reaktionsgleichung

Reaktionsgleichung von HRID 989732
[NH2:1][C:2]1[N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[N:4][C:3]=1[C:18]([NH2:20])=[O:19].[Na].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](OC)=O)=[CH:25][CH:24]=1>C(O)C>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]2[NH:20][C:18](=[O:19])[C:3]3[N:4]=[N:5][N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:2]=3[N:1]=2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 90265Methyl p-tolylacetateHCID 5360545SodiumHCID 11149992HCID 11149992, Verbindung

Produkt 1

HCID 1354846115-(4-Methyl-benzyl)-3-(1-methyl-4-phenyl-butyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrirnidin-7-oneAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1.0 g (3.8 mmol) of 5-amino-1-(1-methyl-4-phenyl-butyl)-1H-[1,2,3]triazole-4-carboxamide are dissolved in a solution of 439 mg of sodium (19 mmol) in 38 ml of ethanol. 2.22 g (14.6 mmol) of methyl 4-methylphenylacetate are added, and the mixture is then refluxed overnight. The solvent is removed under reduced pressure, the residue is taken up with CH2Cl2, the organic phase is extracted twice with 1N HCl and dried over Na2SO4 and the solvent is removed under reduced pressure. Two chromatographic purifications (cyclohexane/ethyl acetate=3:1) give 853 mg (57%) of a solid.

Aufarbeitung

  1. temperaturethe mixture is then refluxed overnight
  2. customThe solvent is removed under reduced pressure
  3. extractionthe organic phase is extracted twice with 1N HCl
  4. dry with materialdried over Na2SO4
  5. customthe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1460cf51abcd4fcea40d48200be58237
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458796B1

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