2-Methoxyethylamine → (2-Methoxy-ethyl)-(5-nitro-pyrazin-2-yl)-amine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.