Potassium Carbonate → 4-[(2,6-Dichloro-9H-purin-9-yl)methyl]benzonitrile

HRID 2170068Notes

Reaction equation

HRID 2170068 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 141986094-[(2,6-Dichloro-9H-purin-9-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-dichloro-9H-purine (16 mmol) is dissolved in DMF (50 mL) and potassium carbonate (50 mmol) is added. α-Bromo-p-tolunitrile (22 mmol) is then added and the mixture is stirred at ambient temperature for 16 hours. After filtration to remove insoluble inorganic salts, the filtrate is poured into water (1500 mL) and extracted with ethyl acetate (2×400 mL), dried over magnesium sulfate and evaporated to yield a residue which is subjected to flash silica gel chromatography using 1:2:10 ethyl acetate/acetone/hexanes. Yield 3.33 g (69%). UV, NMR and MS were consistent with structure assignment.

Workup

  1. filtrationAfter filtration
  2. customto remove insoluble inorganic salts
  3. additionthe filtrate is poured into water (1500 mL)
  4. extractionextracted with ethyl acetate (2×400 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto yield a residue which

Sources & evidence

ORD record
ord-b21414109b8c40898b0e474c05aec652
Source dataset
uspto-grants-2015_06
Patent number
US09050376B2

Reaction notes

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