Water → N-[4-(4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide

HRID 611533Notes

Reaction equation

[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:25]([Cl:27])=[N:24][CH:23]=[N:22][C:21]=3[N:20]([CH:28]([CH3:30])[CH3:29])[CH:19]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C.O>ClCCl>[Cl:27][C:25]1[C:26]2[C:18]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])=[CH:17][CH:16]=3)=[CH:19][N:20]([CH:28]([CH3:30])[CH3:29])[C:21]=2[N:22]=[CH:23][N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzenesulphonyl chloride (0.27 g) in dichloromethane (5 ml) was added dropwise with stirring to a solution of 5-(4-aminophenyl)-4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidine (0.40 g) and triethylamine (155 mg) in dichloromethane (15 ml) at 0° C. under nitrogen. The mixture was stirred at 0° C. for one hour and then warmed to ambient temperature and stirred at this temperature for 18 hours. Water (20 ml) was added and the mixture was extracted with dichloromethane. The combined organic layers were washed with sodium bicarbonate, dried, filtered and evaporated to give N-[4-(4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide

Workup

temperaturewarmed to ambient temperature
stirringstirred at this temperature for 18 hours
extractionthe mixture was extracted with dichloromethane
washThe combined organic layers were washed with sodium bicarbonate
customdried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-ec17fdec137f4630aa6d22648b38799b
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001839

Reaction notes

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