1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-Isothiocyanato-6-(methoxymethyl)pyrimidine

HRID 250045

Reaktionsgleichung

Reaktionsgleichung von HRID 250045
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][O:18][CH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=1>ClCCl>[N:26]([C:22]1[CH:21]=[C:20]([CH2:19][O:18][CH3:17])[N:25]=[CH:24][N:23]=1)=[C:1]=[S:2]

Komponenten

4

Edukt 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 211376446-(Methoxymethyl)-4-pyrimidinamine

Produkt 1

HCID 574765584-Isothiocyanato-6-(methoxymethyl)pyrimidineAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.84 g, 3.59 mmol) was in dichloromethane at ambient temperature was added 6-(methoxymethyl)pyrimidin-4-amine (0.5 g, 3.59 mmol). The orange solution was stirred at ambient temperature for 18 h. The solution was purified by column chromatography (0-40% ethyl acetate/hexanes) to afford 4-isothiocyanato-6-(methoxymethyl)pyrimidine (0.32 g, 1.77 mmol, 49% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.91 (1 H, d, J=1.26 Hz), 7.19 (1 H, d, J=1.01 Hz), 4.52 (2 H, s), 3.49 (3 H, s). MS (LC/MS) R.T.=1.39; [M+H]+=182.10.

Aufarbeitung

  1. customThe solution was purified by column chromatography (0-40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-011b77728d5d45e8aab75daf9408eb75
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863291B2

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