Benzenesulfonyl chloride → 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

HRID 1892133Notes

Reaction equation

HRID 1892133 reaction equation
[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 224845355-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine from step A (1.17 g, 5 mmol) in DMF (10 ml) at 0° C., was added NaH (60% in mineral oil, 0.28 g, 7 mmol). After stirring 15 min., benzensulfonyl chloride (0.64 ml, 5 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 2 hours, resulting in precipitation of a white solid. More DMF (5 ml) was added, and the reaction was quenched with 10 ml of water. The solid was collected by filtration and dried in vacuum to afford 5-bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (1.62 g, 4.35 mmol, 87%) as a white solid, which was carried on without further purification. MS (ES+) [M+H]+=373.

Workup

  1. stirringstirred for 2 hours
  2. customresulting in precipitation of a white solid
  3. customthe reaction was quenched with 10 ml of water
  4. filtrationThe solid was collected by filtration
  5. customdried in vacuum

Sources & evidence

ORD record
ord-53855dffc6eb4baa990f464e952ffba5
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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