Triethylamine → N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine

HRID 502786

Reaktionsgleichung

Br[C:2]1[C:3]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:4][C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23]>[Cu]I.C(#N)C>[CH3:9][NH:8][C:5]1[N:4]=[C:3]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[C:2]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][N:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A 75 mL thick wall glass tube with a teflon screw cap was charged with 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine (0.995 g, 3.68 mmol), acetonitrile (9 mL), triethylamine (3.00 ml, 3.68 mmol), dichlorobistriphenylphosphine palladium(II) (0.259 g, 0.368 mmol), copper(I) iodide (0.0351 g, 0.184 mmol), and ethynyltrimethylsilane (0.362 g, 3.68 mmol). The tube was capped and heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine. MS m/z=288 [M+H]+. Calc'd for C14H17N3SSi: 287.

Aufarbeitung

customThe tube was capped
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag: ord-197ab70497624242988968274d900b34
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07776869B2

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