Sodium hydride → 7-[4-(4-Chlorobenzoyl)benzyl]-3-propyl-7H-pyrrolo-[2,3-d]pyrimidin-4-one

HRID 1291397Notes

Reaction equation

HRID 1291397 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][NH:13][C:7]=2[N:6]=[CH:5]1)[CH2:2][CH3:3].[H-].[Na+].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>COCCOC>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][N:13]3[C:7]4[N:6]=[CH:5][N:4]([CH2:1][CH2:2][CH3:3])[C:9](=[O:10])[C:8]=4[CH:11]=[CH:12]3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 189188723-propyl-7H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 189191847-[4-(4-Chlorobenzoyl)benzyl]-3-propyl-7H-pyrrolo-[2,3-d]pyrimidin-4-oneYield 88.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Under argon gas, 3-propyl-7H-pyrrolo[2,3-d]pyrimidin-4-one (249 mg) was dissolved in anhydrous DME (6 ml) and, under ice-cooling and stirring, 60% sodium hydride-oil (62 mg) was added. The mixture was stirred for 30 minutes, after which a solution of 4-(4-chlorobenzoyl)benzyl bromide (564 mg) in anhydrous DME (2 ml) was added. The mixture was further stirred at room temperature for 2 hours. The solvent was then distilled off under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (silica gel, 21 g; hexane: ethyl acetate =4:1-3:2) to provide the title compound as colorless powder (507 mg).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringThe mixture was further stirred at room temperature for 2 hours
  4. distillationThe solvent was then distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customthe residue was purified by flash column chromatography (silica gel, 21 g; hexane: ethyl acetate =4:1-3:2)

Sources & evidence

ORD record
ord-288e65d9ae444ff9999673be74ab677b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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