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

HRID 854381Notes

Reaction equation

HRID 854381 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.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=3)(=[O:19])=[O:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 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]pyrimidine

Reagents, catalysts & solvents 3

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (Reference: Gerster, John F.; Hinshaw, Barbara C.; Robins, Roland K.; Townsend, Leroy B. Study of electrophylic substitution in the pyrrolo[2,3-d]pyrimidine ring. J. Heterocycl. Chem. (1969), -(2), 207-213) (20 g) and para-toluene sulfonylchloride (28.6 g) in toluene (1L) was treated with a solution of sodium hydroxide (50 g) in water (800 mL), and tetrabutyl ammonium sulfate (462 mg). The solution was stirred vigorously at room temperature for 2 hours and partitioned between ethyl acetate and brine. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a gradient of ethyl acetate and cyclohexane (50:50 to 80:20, v/v) to give the title compound (2.5 g) as a solid m.p.=143° C. LCMS (Method B) RT=2.78 minutes.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-52a406e8e17844239ee41a7df242f517
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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