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

HRID 2097495Notes

Reaction equation

HRID 2097495 reaction equation
CO.[CH3:3][Si:4]([CH3:34])([CH3:33])[CH2:5][CH2:6][O:7][CH2:8][N:9]1[C:13]2[CH:14]=[N:15][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:17](=[O:18])[C:12]=2[C:11]([C:27]#[C:28][Si](C)(C)C)=[CH:10]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>O>[C:27]([C:11]1[C:12]2[C:17](=[O:18])[N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[N:15]=[CH:14][C:13]=2[N:9]([CH2:8][O:7][CH2:6][CH2:5][Si:4]([CH3:33])([CH3:3])[CH3:34])[CH:10]=1)#[CH:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 666033121,5-Bis(2-trimethylsilylethoxymethyl)-3-trimethylsilylethynyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 866270413-Ethynyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 ml of methanol solution containing 10.8 g (22.0 mmol) of 1,5-bis(2-trimethylsilylethoxymethyl)-3-trimethylsilylethynyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 19-(a) was added 1.00 g (7.23 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, water and a saturated aqueous solution of sodium chloride were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 8.58 g of the title compound as a pale yellowish solid. (Yield: 93%)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer after separation
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionthe fractions containing the desired compound
  7. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-227b4352b8904c019eb90bf89b5910f5
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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