5-Benzyloxymethyl-3-methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 3-Methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097504Notes

Reaction equation

HRID 2097504 reaction equation
C(OC[N:10]1[C:15](=[O:16])[C:14]2[C:17]([CH3:28])=[CH:18][N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=2[CH:12]=[N:11]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:28][C:17]1[C:14]2[C:15](=[O:16])[NH:10][N:11]=[CH:12][C:13]=2[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[CH:18]=1

Participants

5

Reactant 2

HCID 666028505-Benzyloxymethyl-3-methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 666030053-Methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 380 ml of ethanol solution containing 25.3 g (65 mmol) of 5-benzyloxymethyl-3-methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 24-(c) was added 25 g of 5% palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 2.5 hours. After completion of the reaction, insoluble material was removed from the reaction suspension by filtration, 100 ml of 28% aqueous ammonia was added to the obtained filtrate, and the mixture was stirred at room temperature for 5 hours. Then, the solution was concentrated under reduced pressure, 500 ml of water was added to the obtained concentrate, and precipitated solid was collected by filtration. The obtained solid was washed with water, and dried under reduced pressure to obtain 14.3 g of the title compound as a pale yellowish solid. (Yield: 79%)

Workup

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed from the reaction suspension by filtration, 100 ml of 28% aqueous ammonia
  3. additionwas added to the obtained filtrate
  4. concentrationThen, the solution was concentrated under reduced pressure, 500 ml of water
  5. additionwas added to the obtained
  6. concentrationconcentrate
  7. customprecipitated solid
  8. filtrationwas collected by filtration
  9. washThe obtained solid was washed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8bee515d16d842b3b220c299e27db2f9
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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