4-Toluenesulfonyl chloride → HCID 23079461, compound

HRID 1684975Notes

Reaction equation

HRID 1684975 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]O)[CH:17]=2)=[C:8]([NH2:24])[N:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:25]([N:27](CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C-]#N.[Na+]>CN(C=O)C.N1C=CC=CC=1>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:25]#[N:27])[CH:17]=2)=[C:8]([NH2:24])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8929Sodium CyanideHCID 23079468HCID 23079468, compound

Product 1

HCID 23079461HCID 23079461, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

2-Butoxy-9-(3-hydroxymethylbenzyl)adenine (0.09 g, 0.27 mmol), triethylamine (0.20 g, 1.98 mmol), tosyl chloride (0.30 g, 1.57 mmol) and pyridine (0.4 ml) were added to DMF (10 ml), and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added sodium cyanide (0.40 g, 9.16 mmol), and the mixture was stirred at 80° C. for 18 hours. After removing the solvent, the residue was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated and the residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1) to give 2-butoxy-9-(3-cyanomethylbenzyl)adenine (0.04 g, 0.12 mmol, yield: 44%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for 18 hours
  2. customAfter removing the solvent
  3. additionthe residue was poured into water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1)

Sources & evidence

ORD record
ord-b8e701a33239417f9fefa8b6ae4ac84e
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

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