Sodium hydride → 5-Ethyl-2-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1291326Notes

Reaction equation

HRID 1291326 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[CH:10]=[N:11][NH:12][C:6]=2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2].[H-].[Na+].[CH3:17][O:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>CN(C=O)C>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[CH:10]=[N:11][N:12]([CH2:29][C:28]3[CH:27]=[CH:26][C:25]([C:23](=[O:24])[C:22]4[CH:33]=[CH:34][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[CH:32][CH:31]=3)[C:6]=2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2].[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2=[CH:10][N:11]([CH2:29][C:28]3[CH:27]=[CH:26][C:25]([C:23](=[O:24])[C:22]4[CH:33]=[CH:34][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[CH:32][CH:31]=3)[N:12]=[C:6]2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 131506704-(4-Methoxybenzoyl)benzyl bromideHCID 18919076HCID 18919076, compound

Product 2

HCID 189188625-Ethyl-2-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 189189835-Ethyl-1-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-ethyl-6-methylthio-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (900 mg) in DMF (20 ml) was added 60% sodium hydride (207 mg) and the mixture was stirred at room temperature for 10 minutes. Then, 4-(4-methoxybenzoyl)benzyl bromide (1.31 g) was added and the mixture was further stirred at room temperature for 30 minutes. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate-chloroform=3:2:1) to provide the title compounds (A) (400 mg) and (B) (366 mg) both as white solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. concentrationThis reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate-chloroform=3:2:1)

Sources & evidence

ORD record
ord-f2021d725b27474aaf83e2c532a583fa
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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