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

HRID 398235Notes

Reaction equation

HRID 398235 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.O>CN(C=O)C>[C:14]1([S:20]([N:4]2[C:5]3[N:6]=[CH:7][N:8]=[C:9]([Cl:11])[C:10]=3[C:2]([Br:1])=[CH:3]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 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 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a slurry of the product from Method T (4.1 g/0.018 mol) in DMF (15 mL) and cooled to 0° C. was added 1.0 g (0.025 mol) of 60% sodium hydride in mineral oil and the resulting mixture stirred at 0° C. for 15 min. Benzenesulfonyl chloride (3.2 g/0.018 mol) was added, the reaction mixture warmed to room temperature and stirred for 2 h. Water was then added (15 mL) and the resulting solid removed by filtration and dried in vacuo affording 5.9 g (89%) of the title compound.

Workup

  1. temperaturethe reaction mixture warmed to room temperature
  2. stirringstirred for 2 h
  3. customthe resulting solid removed by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d00e017a1d1b4dff919358bcecfab200
Source dataset
uspto-grants-2003_08
Patent number
US06610847B2

Reaction notes

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