Toluene → 4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2243370Notes

Reaction equation

HRID 2243370 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C=CC=CC=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineYield 95.6%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 1 l three-necked flask, introduce, with stirring, 11.8 g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 137 ml of toluene, then 16.11 g of 4-methyl-benzenesulphonyl chloride and 5.2 g of tetra-n-butylammonium hydrogen sulphate, then run in, dropwise, 275 ml of an aqueous solution containing 30.7 g of sodium hydroxide. After 30 minutes at room temperature, add 200 ml of ethyl acetate and 200 ml of water. The organic phase is decanted, dried over magnesium sulphate, and concentrated under reduced pressure. After purification by flash chromatography on silica gel, eluting with dichloromethane, we obtain 22.6 g of 4-chloro-7-(4-methylbenzenesulphonyl)-7H-pyrrolo[2,3-d]pyrimidine, in the form of a white solid with the following characteristics:

Workup

  1. additionIn a 1 l three-necked flask, introduce
  2. customThe organic phase is decanted
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash chromatography on silica gel
  6. washeluting with dichloromethane, we

Sources & evidence

ORD record
ord-2a8827552580476793b75170d25eadc0
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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