Ammonium Hydroxide → 3-(5-tert-Butylpyridazin-3-yl)-4-hydroxy-1-methylimidazolidin-2-one

HRID 363988Notes

Reaction equation

HRID 363988 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]([OH:13])[CH2:11][N:10]([CH3:14])[C:9]2=[O:15])=[CH:4][C:3]=1[C:16]([CH3:19])([CH3:18])[CH3:17].[OH-].[NH4+].[H][H]>[Pd].C(O)C>[CH3:19][C:16]([C:3]1[CH:4]=[C:5]([N:8]2[CH:12]([OH:13])[CH2:11][N:10]([CH3:14])[C:9]2=[O:15])[N:6]=[N:7][CH:2]=1)([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 1759313-(5-tert-Butyl-6-chloropyridazin-3-yl)-4-hydroxy-1-methylimidazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1637233-(5-tert-Butylpyridazin-3-yl)-4-hydroxy-1-methylimidazolidin-2-oneYield 122.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.0 g (0.00702 mole) of 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone, 2.0 ml of concentrated ammonium hydroxide, 300 milligrams (mg) of 10% palladium on carbon, and 100 ml of 2B ethanol was placed on a Parr shaker apparatus at 50 pounds of hydrogen. After one hour, when the consumption of hydrogen exceeded the theoretical amount, the mixture was filtered and concentrated, giving 2.15 g of a white solid, which was partitioned between 400 ml of methylene chloride and 40 ml of water. The layers were separated and the organic layer was dried with magnesium sulfate.

Workup

  1. customwhen the consumption of hydrogen
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fb614abbd1fe4932bbe05fe870b19cd5
Source dataset
uspto-grants-1986_08
Patent number
US04604127

Reaction notes

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