2-(2-Hydroxyethyl)pyridine → 4-Furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidin-2-ylamine

HRID 1356073

Reaktionsgleichung

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10](S(C)=O)[N:9]=[C:8]([NH2:15])[N:7]=1.[OH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C1CCN2C(=NCCC2)CC1>COCCOC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:9]=[C:8]([NH2:15])[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a stirred suspension of 500 mg (2.24 mmol) 4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-yl-amine in 20 ml DME was added 0.50 ml (4.48 mmol) 2-(2-hydroxyethyl)pyridine and 0.84 ml (5.60 mmol) DBU and the mixture heated at 100° C. for 72 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether afforded 220 mg (35%) 4-furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidin-2-ylamine as a white crystalline solid. ES-MS m/e (%): 283 (M+H+, 100).

Aufarbeitung

temperatureThe reaction mixture was then cooled to room temperature
custompartitioned between water and dichloromethane
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-3dae4ce8c7d947ba905788575a92f4a6
Quelldatensatz: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06586441B2

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