HCID 54226620, compound → HCID 21960153, compound

HRID 1419008Notes

Reaction equation

HRID 1419008 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[C:21]3[O:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:16][CH:15]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2].[H][H]>O1CCOCC1.[Pd]>[CH2:1]([C:3]1[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH:21]3[O:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:18][CH:19]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 54226620HCID 54226620, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21960153HCID 21960153, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]oxazolidine-2,4-dione (100 mg) (obtained from example 26) in 1,4-dioxane (10 ml) was reduced with hydrogen in the presence of 10% palladium on charcoal (20 mg) at 50 psi for 24 h. The mixture was filtered through a bed of celite. The filtrate was evaporated to dryness under reduced pressure, purified by column chromatography (2:1 EtOAc/petroleum ether as eluent) to afford the title compound (90 mg, 90%).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. custompurified by column chromatography (2:1 EtOAc/petroleum ether as eluent)

Sources & evidence

ORD record
ord-ef1c134ff41745bebe7be2c6a81c0db4
Source dataset
uspto-grants-1999_03
Patent number
US05885997

Reaction notes

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