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 1409597Notes

Reaction equation

HRID 1409597 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 867102972-Cyclohexylmethyl-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl esterYield 70.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-34ac2f912b674fed83b242a76c3ac42f
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

Loading…