5-(4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione → 5-(4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione

HRID 2253646Notes

Reaction equation

HRID 2253646 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH:16]=[C:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:24][CH:25]=1)[C:3]1[N:4]=[CH:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 2

HCID 542274695-(4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 103610445-(4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione (2.4 g) in dry 1,4-dioxan (150 ml) was reduced under hydrogen in the presence of 10% palladium on charcoal (3 g) until hydrogen uptake ceased. The solution was filtered through diatomaceous earth, the filter pad was washed exhaustively with dioxan and the combined filtrates were evaporated to dryness under vacuum. The title compound (mp 150°-51° C.) was obtained after crystallisation from methanol.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. washthe filter pad was washed exhaustively with dioxan
  3. customthe combined filtrates were evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-a64a69417ac84367a0231d226fd9caf2
Source dataset
uspto-grants-1993_08
Patent number
US05232925

Reaction notes

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