Ethanolamine → 2-(5-Nitro-pyrazin-2-ylamino)-ethanol

HRID 719991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719991
Br[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([CH2:13][NH2:14])[OH:12]>CO>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([NH:14][CH2:13][CH2:11][OH:12])=[N:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 140869592-Bromo-5-nitropyrazine

Produkt 1

HCID 218973582-(5-Nitro-pyrazin-2-ylamino)-ethanolAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 2-bromo-5-nitropyrazine (500 mg, 2.45 mmol) and ethanolamine (225 mg, 3.67 mmol) in methanol (15 mL) was stirred at 25° C. for 5 h. After such time, the reaction was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 20/80 hexanes/ethyl acetate to 97/3 ethyl acetate/methanol) afforded 2-(5-nitro-pyrazin-2-ylamino)-ethanol (375 mg, 83%) as a yellow solid: mp 157.5–159.8° C.; EI-HRMS m/e calcd for C6H8N4O3 (M+) 184.0596, found 184.0603.

Aufarbeitung

  1. concentrationAfter such time, the reaction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe9c0629bf034f168ff44b26af8878cc
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132425B2

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