Benzenesulfonyl chloride → HCID 86053731, compound

HRID 1192350Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[Cl:11])[NH:4][N: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>[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])=[N:3]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.3 g, 5.5 mmol) in DMF (42 mL) at 0° C. was added NaH (180 mg, 7.7 mmol) in portions. The reaction mixture was stirred at 0° C. for 5 minutes, then stirred at room temperature for 1.5 hours, after which it was cooled back to 0° C. Neat PhSO2Cl (0.7 mL, 5.6 mmol) was added and the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4Cl and diluted further with H2O. The resulting precipitate was isolated by vacuum filtration to give 1-Benzenesulfonyl-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.8 g, 88%.) 1H NMR (DMSO-d6, 400 MHz) δ 9.11 (1H, s), 8.11 (2H, d, J 8.1 Hz), 7.84 (1H, t, J 7.5 Hz), 7.70 (2H, t, J 8.0 Hz.)

Workup

stirringstirred at room temperature for 1.5 hours
temperatureafter which it was cooled back to 0° C
temperaturethe reaction mixture was warmed to room temperature
stirringstirred overnight
customThe reaction was quenched with saturated aqueous NH4Cl
additiondiluted further with H2O
customThe resulting precipitate was isolated by vacuum filtration

Sources & evidence

ORD record: ord-a148970d63914ad3af69ceacae25a5ad
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680114B2

Reaction notes

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