2-Methoxyethylamine → (2-Methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine

HRID 719988Notes

Reaction equation

HRID 719988 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][O:12][CH2:13][CH2:14][NH2:15]>CO>[CH3:11][O:12][CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 140869592-Bromo-5-nitropyrazine

Product 1

HCID 21897383(2-Methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amineYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-bromo-5-nitropyrazine (500 mg, 2.45 mmol) and 2-methoxyethylamine (276 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, 2/3 to 1/4 hexanes/ethyl acetate) afforded (2-methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine (291 mg, 60%) as a yellow solid: mp 116.0–117.3° C.; EI-HRMS m/e calcd for C7H10N4O3 (M+) 198.0753, found 198.0751.

Workup

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

Sources & evidence

ORD record
ord-a04a4c8a4eac402e9728e0a5a9301698
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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