Trimethylsilylacetylene → 4-{2-Methyl-6-[2-(trimethylsilyl)ethynyl]-1,3-benzodiazol-1-yl}-1,3,5-triazin-2-amine

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Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C(N(CC)CC)C>[CH3:10][C:8]1[N:7]([C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[C:6]2[CH:18]=[C:2]([C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=[CH:4][C:5]=2[N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a mixture of 4-(6-bromo-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine (250 mg, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol), copper(I) iodide (11 mg, 0.06 mmol) and ethynyl(trimethyl)silane 0.230 ml, 1.51 mmol) was added triethylamine (2.6 mL). The mixture was purged with nitrogen for 2 minutes and was stirred at 80° C. for 15 min in the microwave. LC-MS shows 50% conversion. The mixture was retreated with another equivalent of tetrakis(triphenylphosphine)palladium (70 mg) copper(I) iodide (11 mg) and ethynyl(trimethyl)silane (0.230 ml). Heating in the microwave at 90° C. was continued for another

Aufarbeitung

customThe mixture was purged with nitrogen for 2 minutes
temperatureHeating in the microwave at 90° C.

Quellen und Nachweise

ORD-Eintrag: ord-36a62ea70dac43158d5e362abc007cd7
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08901313B2

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