Sodium Carbonate → 2-(4-(4-(Benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile

HRID 1484836

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 4-(benzyloxy)-2-chloropyrimidine (3.2 g, 14.5 mmol, 1.0 equiv.), 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (4.2 g, 17.4 mmol, 1.2 equiv.), Pd(dippf)Cl2 (1.18 g, 1.45 mmol, 0.1 equiv.), Na2CO3 (6.1 g, 58 mmol, 4.0 equiv.), dioxane (5 ml) and water (1 ml) was added to the filtrate. The reaction mixture was heated to 100° C. for 15 h under nitrogen atmosphere. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 200:1) to afford 2-(4-(4-(benzyloxy)pyrimidin-2-yl)phenyl)acetonitrile (1.3 g, 31%) as white solid. The title compound was determination by LC-MS (LC-MS (m/z)=302.1 [M+H]+).

Aufarbeitung

additionwas added to the filtrate
customThe residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 200:1)

Quellen und Nachweise

ORD-Eintrag: ord-e84f68b1f54d49de942bbf9481d80bc8
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09422271B2

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