Water → HCID 20061121, compound

HRID 1085280Notes

Reaction equation

HRID 1085280 reaction equation
Cl.[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[O:28]CC=C)[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:32])[N:5]([CH3:33])[C:4]1=[O:34].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO.[Pd]>[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[OH:28])[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:32])[N:5]([CH3:33])[C:4]1=[O:34]

Participants

6

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 20061446HCID 20061446, compound2×

Product 1

HCID 20061121HCID 20061121, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.6 g of 1,3-dimethyl-6-{4-[3-(2-allyloxy-4-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione (Compound 161--free form) was dissolved in 10 ml of methanol, followed by the addition of 0.1 g of 10% Pd/activated carbon, 0.1 g of p-toluenesulfonic acid monohydrate and 2 ml of water. The resultant mixture was heated for 15 hours under stirring and reflux. After allowing the reaction mixture to cool down, insoluble matters were filtered off and the filtrate was concentrated. The residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=50/1, by volume), thereby thereby obtaining 0.4 g of 1,3-dimethyl-6-{4-[3-(2-hydroxy-4-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperaturereflux
  2. temperatureto cool down
  3. filtrationinsoluble matters were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=50/1, by volume)

Sources & evidence

ORD record
ord-b388d57f0dce4cb38ea2b27e6b88b0ad
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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