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

HRID 719991Notes

Reaction equation

HRID 719991 reaction equation
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]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 140869592-Bromo-5-nitropyrazine

Product 1

HCID 218973582-(5-Nitro-pyrazin-2-ylamino)-ethanolYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fe9c0629bf034f168ff44b26af8878cc
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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