Ethylene Glycol → 4,6-Diamino-2-(2-hydroxy-ethoxy)-nicotinonitrile

HRID 1364522

Reaktionsgleichung

[CH2:1]([OH:4])[CH2:2][OH:3].[Na].Br[C:7]1[N:14]=[C:13]([NH2:15])[CH:12]=[C:11]([NH2:16])[C:8]=1[C:9]#[N:10]>O>[NH2:16][C:11]1[C:8]([C:9]#[N:10])=[C:7]([O:3][CH2:2][CH2:1][OH:4])[N:14]=[C:13]([NH2:15])[CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A heavy walled, sealable tube suitable for microwave heating was charged with 3 mL of ethylene glycol and 50 mg (2.2 mmol) of sodium. The mixture was stirred at 95° C. until all of the sodium had reacted, then 213 mg (1.00 mmol) of 2-bromo-4,6-diaminonicotinonitrile was added. The tube was sealed, and the mixture was heated with a microwave apparatus at 150° C. for 10 minutes then cooled. The mixture was diluted with 15 mL of water, and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate layers were back extracted with water (1×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to provide 85 mg (44%) of a solid. 1H NMR (300 MHz, d6-DMSO) δ 6.20 (s, 2H), 6.16 (s, 2H), 5.32 (s, 1H), 4.76 (t, 1H, J=5.3 Hz), 4.21 (m, 2H), 3.64 (q, 2H, J=5.4 Hz); MS (ESI) m/e=151 (M−EtOH+H)+, 195 (M+H)+.

Aufarbeitung

temperatureA heavy walled, sealable tube suitable for microwave heating
customhad reacted
customThe tube was sealed
temperaturethen cooled
extractionextracted with ethyl acetate (3×5 mL)
extractionThe combined ethyl acetate layers were back extracted with water (1×5 mL), and brine (1×5 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-50476bb8a5e04de08eb6063c93445ab3
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07888374B2

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