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

HRID 1853383Notes

Reaction equation

HRID 1853383 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:13]1[N:14]=[C:15]([Cl:22])[C:16]2[CH:21]=[CH:20][NH:19][C:17]=2[N:18]=1.[OH-].[Na+]>CC(C)=O>[Cl:22][C:15]1[C:16]2[CH:21]=[CH:20][N:19]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[C:17]=2[N:18]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineYield 104.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Methylbenzene-1-sulfonyl chloride (3.7 g, 19.32 mmol, 1.20 equiv.) was added to a solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 1 (3 g, 16.1 mmol, 1.00 equiv.) in acetone (20 mL). At about 0° C., an aqueous sodium hydroxide solution (2 mol/L, 12 mL) was added dropwise to the solution. The solution was then stirred at ambient temperature for about 3 hours. The solids were collected by filtration and washed with acetone/water to give the title product as a white solid (5.2 g; yield=95%). LC-MS: m/z=342 (M+H)+.

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with acetone/water

Sources & evidence

ORD record
ord-43c140d2712f4bfc84024c56370d3b8a
Source dataset
uspto-grants-2015_02
Patent number
US08962638B2

Reaction notes

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