Bromine → 3-Amino-6-bromopyrazine-2-carboxamide

HRID 2201570Notes

Reaction equation

HRID 2201570 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.CC([O-])=O.[Na+].[Br:16]Br>CC(O)=O>[NH2:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][C:5]([Br:16])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 280292Aminopyrazine carboxamideHCID 517045Sodium Acetate

Product 1

HCID 4708993-Amino-6-bromopyrazine-2-carboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-aminopyrazine-2-carboxamide (1 g, 7.24 mmol, prepared according to International Patent Application Publication No. WO2011054922) and NaOAc (200 mg, 2.44 mmol) in HOAc (15 mL) was added Br2 (0.45 mL) dropwise at 0° C. for 1 hour, and then it was stirred at 50° C. for 8 hours. After the mixing, it was poured into ice-water and filtrated, the crude product of 3-amino-6-bromopyrazine-2-carboxamide as brown solid (1.5 g, yield: 95%) was obtained. 1H-NMR (DMSO-d6, 400 MHz) δ 8.30 (s, 1H), 7.93 (s, 2H), 7.66 (s, 2H). MS (M+H)+: 217/219.

Workup

  1. filtrationfiltrated

Sources & evidence

ORD record
ord-2a914bcbf20e4df0a7dbaf10d9f167cb
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

Loading…