Sodium hydride → HCID 18919322, compound

HRID 1291262Notes

Reaction equation

HRID 1291262 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[N:12][C:5]=2[NH:4][C:3]1=[S:13].[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>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][S:13][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[C:6]4[CH:9]=[CH:10][CH:11]=[N:12][C:5]=4[N:4]=3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 14613674HCID 14613674, compound

Product 1

HCID 18919322HCID 18919322, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-methylpyrido[2,3-d]pyrimidin-4-one-2-thione (193 mg) in DMF (5 ml) were added sodium hydride (60 mg) and 4-(4-chlorobenzoyl)benzyl bromide (310 mg) and the mixture was stirred at room temperature for 30 minutes. The reaction mixtrue was then diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was then distilled off. The residue was recrystallized (ethyl acetate-ether-hexane) to provide the title compound as white powder (162 mg, 38%). 1H-NMR (CDCl3) δ: 3.62(3H,s), 4.73(2H,s), 7.26-7.79(9H,m), 8.54-8.61(1H,m), 8.90-8.95(1H,m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off
  5. customThe residue was recrystallized (ethyl acetate-ether-hexane)

Sources & evidence

ORD record
ord-2ccf128046c64924b3e5b849c7b3fd72
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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