N-Methylethylenediamine → 3,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide

HRID 1165438Notes

Reaction equation

HRID 1165438 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([O:12]C)=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[CH3:14][NH:15][CH2:16][CH2:17][NH2:18]>O1CCCC1>[NH2:1][C:2]1[C:3]([C:10]([NH:18][CH2:17][CH2:16][NH:15][CH3:14])=[O:12])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

4

Reactant 2

HCID 8014N-MethylethylenediamineHCID 73827Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Product 1

HCID 198618223,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamideYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 20 g (99.0 mmol) of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (see U.S. Pat. No. 4,029,816 for an example of how to obtain this material) and 17 g (230.0 mmol) of N-methylethylenediamine was heated at reflux under an inert atmosphere for 30 hours. The rection mixture was cooled to ambient temperature and the solid was dissolved in 100 ml of tetrahydrofuran. The solution was filtered and evaporated. The residue was crystallized from 2-propanol. There was obtained 15.0 g (61.2 mmol, 61%) of 3,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide; mp 142.5°-143° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an inert atmosphere for 30 hours
  3. filtrationThe solution was filtered
  4. customevaporated
  5. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-78c67c5d94084f14ada9ce2cbb35759a
Source dataset
uspto-grants-1990_03
Patent number
US04910202

Reaction notes

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