5-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dione → 5-[4-[2-[4-methyl-2-Propyl-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione

HRID 382292Notes

Reaction equation

HRID 382292 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:26][CH2:27][CH3:28])[N:5]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:14][CH:13]=2)[C:6](=[O:8])[CH:7]=1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([CH2:26][CH2:27][CH3:28])[N:5]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:17]=2)[C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 2

HCID 539648275-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 154909495-[4-[2-[4-methyl-2-Propyl-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dioneYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione (5.0 g, 12.46 mmol) obtained from example 1 in 1,4-dioxane (75 ml) was reduced with hydrogen in the presence of 10% palladium on charcoal (12.0 g) at 60 psi pressure for 40 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) followed by crystallisation (CH2Cl2) to afford the title compound (4.6 g, 92%), mp 144-146° C.

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)
  4. customfollowed by crystallisation (CH2Cl2)

Sources & evidence

ORD record
ord-42da439e071342f7a5fe7ee18486253b
Source dataset
uspto-grants-2001_10
Patent number
US06310069B1

Reaction notes

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