Triethylsilane → 1-Benzyloxymethyl-3-isopropyl-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one

HRID 2097501Notes

Reaction equation

HRID 2097501 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:15][CH2:16][N:17]1[C:21]2[CH:22]=[N:23][NH:24][C:25](=[O:26])[C:20]=2[C:19]([C:27](O)([CH3:29])[CH3:28])=[CH:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:8]([O:15][CH2:16][N:17]1[C:21]2[CH:22]=[N:23][NH:24][C:25](=[O:26])[C:20]=2[C:19]([CH:27]([CH3:29])[CH3:28])=[CH:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666032561-Benzyloxymethyl-3-(1-hydroxy-1-methylethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666025541-Benzyloxymethyl-3-isopropyl-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-oneYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 13 ml of dichloromethane solution containing 2.47 g of triethylsilane was added 1.31 ml of boron trifluoride diethyl ether complex under ice-cooling, then 30 ml of dichloromethane solution containing 1.65 g (5.3 mmol) of 1-benzyloxymethyl-3-(1-hydroxy-1-methylethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 21-(d) was added dropwise to the mixture, and the mixture was stirred at room temperature for 22 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, and the mixture was extracted with chloroform. 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; toluene:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.98 g of the title compound as a white solid. (Yield: 62%)

Workup

  1. additionwas added 1.31 ml of boron trifluoride diethyl ether complex under ice-
  2. temperaturecooling
  3. addition21-(d) was added dropwise to the mixture
  4. customAfter completion of the reaction
  5. extractionthe mixture was extracted with chloroform
  6. customThe organic layer after separation
  7. washwas washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionthe fractions containing the desired compound
  11. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-edb7c43ff0014556955372f8d011cf6c
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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