HCID 66602977, compound → HCID 66602683, compound

HRID 2097547Notes

Reaction equation

HRID 2097547 reaction equation
O[CH:2]([C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:11]=[CH:10][C:9]=2[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:7]=1)[CH2:3][O:4]C.[H][H]>[C].[Pd].C(O)(=O)C>[OH:4][CH2:3][CH2:2][C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[N:11]=[CH:10][C:9]=2[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[CH:7]=1

Participants

5

Reactant 2

HCID 66602977HCID 66602977, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66602683HCID 66602683, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To 40 ml of acetic acid solution containing 2.30 g (4.90 mmol) of 3-(1-hydroxy-2-methoxyethyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 57-(d) was added 1.0 g of 10% palladium-carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at 80° C. for 2.5 hours. After completion of the reaction, insoluble material was filtered off from the reaction mixture, and the filtrate was concentrated under reduced pressure. Water was added to the residue, the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=3:7 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.43 g of the title compound as a colorless oil. (Yield: 66%)

Workup

  1. customAfter completion of the reaction, insoluble material
  2. filtrationwas filtered off from the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionthe fractions containing the desired compound
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-30f3cee856354d0f9fe145230fabb445
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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