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

HRID 2097516Notes

Reaction equation

HRID 2097516 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:19])[C:13]=2[CH:12]=[C:11]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C(=O)([O-])[O-].[K+].[K+].[H][H]>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:19])[C:13]=2[CH:12]=[CH:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66602722HCID 66602722, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 666031011-Benzyloxymethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 195.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To 5.00 g (10.8 mmol) of 1-benzyloxymethyl-2-bromo-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one obtained in Reference example 33-(a) were added 50 ml of methanol, 30 ml of toluene, 1.5 g of potassium carbonate and 2.5 g of 51 palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 3 hours. After completion of the reaction, insoluble material of the reaction suspension was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; toluene:ethyl acetate=1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 8.15 g of the title compound as a pale yellowish solid. (Yield: 77%)

Workup

  1. customAfter completion of the reaction, insoluble material of the reaction suspension
  2. customwas removed 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-cee5ca4f9dc94da3936ad30ba4dc0a28
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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