Diisopropylethylamine → 4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

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Reaktionsgleichung

[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18](Cl)[C:13]=3[C:12]([Br:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>CC(O)C>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:18]2[C:13]3[C:12]([Br:20])=[CH:11][N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A suspension of 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.9 g, 13 mmol), Piperazine-1-carboxylic acid tert-butyl ester (3.7 g, 20 mmol), and DIPEA (5.7 mL, 33 mmol) in IPA (30 mL) was stirred and heated at reflux for 6 hours. The mixture was cooled to −10° C., the solids collected by vacuum filtration, rinsed with cold IPA and dried under vacuum to give 4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (5.9 g, 86%.) LCMS (APCI+) m/z 522 and 524 [M+H]+; Rt: 3.92 min. 1H NMR (DMSO-d6, 400 MHz) δ 8.48 (1H, s), 8.21 (2H, d, J 8.2 Hz), 7.66-7.62 (2H, m), 7.54 (2H, t, J 7.8 Hz), 3.62-3.55 (8H, m), 1.48 (9H, s.)

Aufarbeitung

temperatureheated
temperatureat reflux for 6 hours
filtrationthe solids collected by vacuum filtration
washrinsed with cold IPA
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-3d4f47300773422282eda8e3a6ba7966
Quelldatensatz: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08680114B2

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