Hydrochloric Acid → 2,6-Dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1h-pyrrolo[3,4-d]pyridazin-1-one

HRID 1835148Notes

Reaction equation

HRID 1835148 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][NH:10][CH:11]=[C:5]2[C:4]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:3]1.[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[I-].[K+].Cl>CN(C)C=O>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:11]=[C:5]2[C:4]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:3]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1355247842-methyl-4-(2-methylpropyl)-1H,2H,6H-pyrrolo[3,4-d]pyridazin-1-one

Product 1

HCID 235032512,6-Dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1h-pyrrolo[3,4-d]pyridazin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2,6-dihydro-2-methyl-4-(2-methylpropyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (0.65 g) in dry dimethyl formamide (3 ml) was added dropwise to sodium hydride (0.15 g of a 60% dispersion in oil) in dimethyl formamide (10 ml) with stirring. After 20 minutes benzyl bromide (0.45 ml) and a crystal of potassium iodide were added. The mixture was stirred for 11 days and then poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The organic phase was washed with water, dried, and evaporated to give an oil, which was purified by chromatography on silica (ethyl acetate/isohexane 3:1) to afford, after crystallisation from cyclohexane, 2,6-dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1H-pyrrolo[3,4-d]pyridazin-1-one (0.3 g).

Workup

  1. stirringThe mixture was stirred for 11 days
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated
  6. customto give an oil, which
  7. customwas purified by chromatography on silica (ethyl acetate/isohexane 3:1)
  8. customto afford
  9. customafter crystallisation from cyclohexane, 2,6-dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1H-pyrrolo[3,4-d]pyridazin-1-one (0.3 g)

Sources & evidence

ORD record
ord-3ee0bfd766d34579834f01eac3a5d40a
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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