Tetrahydrofuran → 1-Benzyloxymethyl-3-(1-hydroxy-1-methylethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097500Notes

Reaction equation

HRID 2097500 reaction equation
O1CCC[CH2:2]1.[C:6]([C:9]1[C:17]2[C:16](=[O:18])[NH:15][N:14]=[CH:13][C:12]=2[N:11]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1)(=[O:8])[CH3:7].C[Mg]Br.[Cl-].[NH4+]>C(OCC)C>[CH2:21]([O:20][CH2:19][N:11]1[C:12]2[CH:13]=[N:14][NH:15][C:16](=[O:18])[C:17]=2[C:9]([C:6]([OH:8])([CH3:2])[CH3:7])=[CH:10]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 666027273-Acetyl-1-benzyloxymethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 666032561-Benzyloxymethyl-3-(1-hydroxy-1-methylethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 87 ml of tetrahydrofuran solution containing 1.69 g (5.7 mmol) of 3-acetyl-1-benzyloxymethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 21-(c) was added dropwise 7.5 ml of 3M methyl magnesium bromide in diethyl ether solution under ice-cooling, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was 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; toluene:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.66 g of the title compound as a white solid. (Yield: 93%)

Workup

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

Sources & evidence

ORD record
ord-8eafbe03ee5e44f39ac6b367da5dd6fd
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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