Ethanol → 3-Ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097496Notes

Reaction equation

HRID 2097496 reaction equation
[C:1]([C:3]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:8]=[CH:7][C:6]=2[N:5]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:4]=1)#[CH:2].C(O)C.[H][H]>[Pd].O1CCCC1>[CH2:1]([C:3]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[N:8]=[CH:7][C:6]=2[N:5]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 866270413-Ethynyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 666029623-Ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 8.56 g (20.4 mmol) of 3-ethynyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 19-(b) were added 300 ml of ethanol and 200 ml of tetrahydrofuran, then, 2.0 g of 5% palladium-active carbon was added to the mixture, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 15 hours. After completion of the reaction, insoluble material was removed from the reaction suspension by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1→4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 8.00 g of the title compound as a pale yellowish solid. (Yield: 93%)

Workup

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed from the reaction suspension by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionthe fractions containing the desired compound
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf7a3a24cc814a37b8a29516f38e794a
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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