Sodium hydride → 2-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-2,3-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochloride

HRID 1291325Notes

Reaction equation

HRID 1291325 reaction equation
[K].[CH2:2]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[N:12][NH:13][C:7]=2[N:6]=[C:5]1[SH:14])[CH3:3].C[O-].[Na+].[ClH:18].[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][Cl:24].[H-].[Na+].[Cl:28][C:29]1[CH:44]=[CH:43][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=2)=[O:34])=[CH:31][CH:30]=1>CN(C=O)C>[ClH:24].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39][N:13]3[C:7]4[N:6]=[C:5]([S:14][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[N:4]([CH2:2][CH3:3])[C:9](=[O:10])[C:8]=4[CH:11]=[N:12]3)=[CH:37][CH:36]=2)=[O:34])=[CH:43][CH:44]=1.[ClH:18].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39][N:12]3[CH2:11][C:8]4[C:9](=[O:10])[N:4]([CH2:2][CH3:3])[C:5]([S:14][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])=[N:6][C:7]=4[NH:13]3)=[CH:37][CH:36]=2)=[O:34])=[CH:43][CH:44]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 10942334Sodium MethoxideHCID 178462982HCID 178462982, compound

Product 2

HCID 189188292-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-2,3-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochlorideHCID 189192861-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-1,5-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-ethyl-6-mercapto-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one potassium (2.0 g) in DMF (25 ml) was added 28% sodium methoxide (1.75 ml). Then, 3-dimethylaminopropyl chloride hydrochloride (1.62 g) was added and the mixture was stirred at 60° C. for 1 day. To this reaction mixture was added 60% sodium hydride (232 mg) and the mixture was stirred at room temperature for 10 minutes. Thereafter, 4-(4-chlorobenzoyl)benzyl bromide (1.778 g) was added and the reaction mixture was 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 (chloroform: methanol: concentrated aqueous ammonia=50:1:0.1) and treated with hydrogen chloride/ethyl acetate to provide the title compound (A) (518 mg) and (B) (262 mg) both as colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. concentrationThis reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform: methanol: concentrated aqueous ammonia=50:1:0.1)
  9. additiontreated with hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-c45b89f721d944f3b9771460643d568c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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