Benzenesulfonyl chloride → 4-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527991Notes

Reaction equation

[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-bromo-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 12.62 mmol) in 50 mL N,N-dimethylformamide at 0° C. was added 95% sodium hydride (0.351 g, 13.89 mmol). The mixture was stirred at 0° C. for 30 minutes, benzenesulfonyl chloride (1.772 mL, 13.89 mmol) was added, and the mixture was stirred at 0° C. for an additional 2 hours. The mixture was quenched with 20 mL saturated ammonium chloride and diluted with water (100 mL). The resulting suspension was stirred for 5 minutes, filtered, and dried under-vacuum to give the title compound. MS (ESI+) m/z 340.0 (M+H)+.

Workup

stirringthe mixture was stirred at 0° C. for an additional 2 hours
customThe mixture was quenched with 20 mL saturated ammonium chloride
additiondiluted with water (100 mL)
stirringThe resulting suspension was stirred for 5 minutes
filtrationfiltered
customdried under-vacuum

Sources & evidence

ORD record: ord-bbb9ead34179480c8fd333bb1d516ccc
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346813B2

Reaction notes

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