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

HRID 334174Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[C:14]1([S:20]([N:8]2[C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:11])[C:5]=3[CH:10]=[CH:9]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1 g, 5.3 mmol) in anhydrous THF (5 mL) was added to a suspension of sodium hydride (234 mg, 5.83 mmol, 60% dispersion in mineral oil) in anhydrous THF (15 mL) at 0° C. The resulting mixture was stirred at 0° C. for 45 min, and benzenesulfonyl chloride (1.12 g, 6.36 mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature and stirred at RT for 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated with cyclohexane affording 7-Benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid (1.52 g, 87%). 1H NMR (400 MHz, CDCl3): δ 8.24 (2H, m), 7.76 (1H, d, J=4.0 Hz), 7.69 (1H, m), 7.58 (2H, m), 6.69 (1H, d, J=4.0 Hz).

Workup

temperatureto warm to ambient temperature
stirringstirred at RT for 1 h
customThe reaction mixture was quenched with saturated aqueous ammonium chloride
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was triturated with cyclohexane

Sources & evidence

ORD record: ord-af02deb7e66542dbbee268c0757e3a7b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883799B2

Reaction notes

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