Chlorine → Methyl 3-amino-6-chloropyrazine-2-carboxylate

HRID 128138Notes

Reaction equation

HRID 128138 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:12]Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([Cl:12])=[CH:4][N:3]=1.[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][C:5]([Cl:12])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 2

HCID 824637Methyl 3-amino-6-chloropyrazine-2-carboxylateHCID 128084192-Amino-5-chloropyrazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

One of the intermediates, 2-amino-5-chloropyrazine is prepared following the general procedure of Palamidessi and Bernardi, J. Org. Chem. 29, 2491 (1964), wherein methyl 2-amino-3-pyrazinylcarboxylate is allowed to react with chlorine in acetic acid to yield methyl 2-amino-5-chloro-3-pyrazinylcarboxylate. This ester is hydrolyzed with aqueous sodium hydroxide to yield 2-amino-3-carboxy-5-chloropyrazine, which is then heated in tetrahydronaphthalene and decarboxylated to yield the desired 2-amino-5-chloropyrazine.

Sources & evidence

ORD record
ord-8dab6a5a64e14357abefad176c504460
Source dataset
uspto-grants-1981_03
Patent number
USRE030563

Reaction notes

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