Triethylamine → 3,3'-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

HRID 75418

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([N:17]2[CH2:23][CH:22]3[O:24][CH:19]([CH2:20][CH2:21]3)[CH2:18]2)[CH:3]=1.Cl.[CH:26]12[O:33][CH:30]([CH2:31][CH2:32]1)[CH2:29][NH:28][CH2:27]2.C(N(CC)CC)C.CCN(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]([N:17]3[CH2:23][CH:22]4[O:24][CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[CH:3]=[C:2]([N:28]3[CH2:27][CH:26]4[O:33][CH:30]([CH2:31][CH2:32]4)[CH2:29]3)[N:7]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

In a 100 mL round-bottomed flask was placed 3-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (13, 135 mg, 0.39 mmol) in dioxane (5 ml). 8-Oxa-3-azabicyclo[3.2.1]octane, HCl (2, 0.15 g, 1 mmol) and triethylamine (0.28 ml, 2 mmol) were added. The mixture was stirred at 80° C. for 16 hours. DIPEA was added (0.3 mL) and stirring was continued at 80° C. for 64 hours. The reaction mixture was diluted with ethyl acetate and washed with sat NaHCO3 followed by 0.1 N HCl. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was added to a silica gel column and eluted with ethyl acetate in hexanes (10-50%) to give 65 mg of the title compound (0.15 mmol, 39%).

Aufarbeitung

customIn a 100 mL round-bottomed flask was placed
stirringstirring
waitwas continued at 80° C. for 64 hours
washwashed with sat NaHCO3
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
additionThe crude product was added to a silica gel column
washeluted with ethyl acetate in hexanes (10-50%)

Quellen und Nachweise

ORD-Eintrag: ord-384148ab9b8943aebdf4aaf364254858
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835429B2

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