N-bromobutanimide → Methyl 3-Amino-6-bromopyrazine-2-carboxylate

HRID 2174657Notes

Reaction equation

HRID 2174657 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][C:5]([Br:12])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-aminopyrazine-2-carboxylate (100 g, 653.0 mmol) and N-bromosuccinimide (116.2 g, 653.0 mmol) were stirred in MeCN (1.198 L) at ambient temperature for 15 hours. The resultant precipitate was isolated by filtration and washed with MeCN (10 mL) and diethyl ether (100 mL) to give the sub-title product as pale yellow flakes (123.73 g, 82% Yield). 1H NMR (400.0 MHz, CDCl3) δ 4.00 (s, 3H), 6.47 (br s, 2H), 7.28 (s, 1H) and 8.31 (s, 1H) ppm; (ES+) 232.0.

Sources & evidence

ORD record
ord-93851dc6144042509f5f8c6622d09ebd
Source dataset
uspto-grants-2015_06
Patent number
US09062008B2

Reaction notes

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