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

HRID 1807346Notes

Reaction equation

HRID 1807346 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-d81e934773b04a7da01cd6a8bf6b9e16
Source dataset
uspto-grants-2013_01
Patent number
US08357374B2

Reaction notes

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