Isoquinolin-3-Amine → 3-Isothiocyanatoisoquinoline

HRID 250056

Reaktionsgleichung

Reaktionsgleichung von HRID 250056
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]([NH2:27])[N:18]=1>ClCCl>[N:27]([C:19]1[N:18]=[CH:17][C:26]2[C:21]([CH:20]=1)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:1]=[S:2]

Komponenten

4

Edukt 2

HCID 311869Isoquinolin-3-AmineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridone

Produkt 1

HCID 574765653-Isothiocyanatoisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.805 g, 3.47 mmol) in dichloromethane at room temperature was added isoquinolin-3-amine (0.5 g, 3.47 mmol). The reaction was stirred at room temperature for 18 hours. The LC/MS showed the desired product peak a major peak. The deep orange solution was concentrated and filtered. The filtrate was purified by silica gel chromatography (0-40% ethyl acetate-hexanes) to afford 4-isothiocyanato-6-(3-methoxyphenyl)pyrimidine (0.55 g, 2.96 mmol, 85% yield) a white solid. LCMS R.T.=2.47; [M+H]+=187.23.

Quellen und Nachweise

ORD-Eintrag
ord-c02849d85d56466aa5c8f18a5640e9f9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863291B2

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