5-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester → 2-Cyclohexylmethyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester

HRID 1409597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409597
C([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:11][C:10]=1[C:24]([O:26][CH3:27])=[O:25])C1C=CC=CC=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:27][O:26][C:24]([C:10]1[N:11]=[C:12]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:13]([CH3:16])[C:14](=[O:15])[C:9]=1[OH:8])=[O:25]

Komponenten

4

Edukt 1

HCID 867102965-Benzyloxy-2-cyclohexylmethyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid methyl ester

Produkt 1

HCID 867102972-Cyclohexylmethyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl esterAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-(benzyloxy)-2-(cyclohexylmethyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate (60 mg, 162 μmol) and 20% palladium hydroxide on carbon (11.4 mg, 16.2 μmol) in EtOAc (10 ml) was placed under an atmosphere of hydrogen and stirred at room temperature overnight. The mixture was filtered and then evaporated to dryness. Chromatography (SiO2; 0 to 20% EtOAc in hexanes) gave the title product as a white solid (0.032 g; 70%). LCMS: m/z=281 (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-34ac2f912b674fed83b242a76c3ac42f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921388B2

Notizen zur Reaktion

Wird geladen…