3-(Phenylsulfonyl)pyrrolidine → 5-{9-(Cyclopropylmethyl)-6-morpholin-4-yl-8-[3-(phenylsulfonyl)pyrrolidin-1-yl]-9H-purin-2-yl}pyrimidin-2-amine

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Reaktionsgleichung

[C:1]1([S:7]([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:16]1[N:17]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:18]2[C:23]([N:24]=1)=[C:22]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[N:21]=[C:20]([C:31]1[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=1)[N:19]=2>CS(C)=O>[CH:39]1([CH2:38][N:17]2[C:16]([N:12]3[CH2:13][CH2:14][CH:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH2:11]3)=[N:24][C:23]3[C:18]2=[N:19][C:20]([C:31]2[CH:36]=[N:35][C:34]([NH2:37])=[N:33][CH:32]=2)=[N:21][C:22]=3[N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH2:40][CH2:41]1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

3-(Phenylsulfonyl)pyrrolidine (110 mg, 0.52 mmol) and dimethyl sulfoxide (0.8 ml) were added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine (80 mg, 0.21 mmol) and the resulting mixture was stirred at 150° C. for 4 hours. The reaction mixture was partitioned with ethyl acetate and water and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1) to give the title compound (20 mg, 17%) as a white solid.

Aufarbeitung

customThe reaction mixture was partitioned with ethyl acetate and water
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1)

Quellen und Nachweise

ORD-Eintrag: ord-0d6934cbb62e4987962d1aa74f928d5e
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08097622B2

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