Tetrahydrofuran → HCID 86686212, Verbindung

HRID 1021242

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C1COCC1.C([Li])CCC.CCCCCC.[N:33]1([C:39]2[N:44]=[CH:43][C:42]([CH:45]=[O:46])=[CH:41][N:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CCOC(C)=O.O>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:45]([C:42]2[CH:43]=[N:44][C:39]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[N:40][CH:41]=2)[OH:46])[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

[(3-Bromobenzyl)oxy](tert-butyl)dimethylsilane (860 mg) was mixed with THF (10 ml), followed by cooling to −78° C. under argon atmosphere. A 1.60 M n-butyl lithium/hexane solution (1.8 ml) was added dropwise thereto, followed by stirring at −78° C. for 10 minutes, and then 2-morpholin-4-ylpyrimidine-5-carboaldehyde (500 mg) was added thereto. The mixture was warmed to 0° C. over 1 hour and then stirred again at 0° C. for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol (914 mg).

Aufarbeitung

temperatureThe mixture was warmed to 0° C. over 1 hour
stirringstirred again at 0° C. for 1 hour
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-d1602688f92f4cfea67bb4f975b75015
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08716470B2

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