Cesium carbonate → tert-butyl 5-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate

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Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.[CH3:25][N:26]1[CH:30]=[C:29]([NH2:31])[N:28]=[CH:27]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:31][C:29]2[N:28]=[CH:27][N:26]([CH3:25])[CH:30]=2)=[N:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a suspension of tert-butyl 5-[(2,5-dichloropyrimidin-4-yl)amino]-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (373.0 mg, 1.00 mmol) and 1-methylimidazol-4-amine (341.8 mg, 3.52 mmol) in dioxane (10 mL) were added Pd(OAc)2 (52.0 mg, 0.23 mmol), BINAP (125.0 mg, 0.19 mmol) and Cs2CO3 (647.2 mg, 1.99 mmol). The reaction mixture was stirred at 150° C. under microwave for 2 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50) to give the title compound as a pale yellow solid (0.21 g, 48%).

Aufarbeitung

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50)

Quellen und Nachweise

ORD-Eintrag: ord-003bd9714fbe43df9572207a0da3282d
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09403801B2

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