Benzylamine → 5-Chloro-3-[(benzylimino)methyl]-6-(methylthio)pyrazineamine

HRID 2164762Notes

Reaction equation

HRID 2164762 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[N:6][C:5]([Cl:10])=[C:4]([S:11][CH3:12])[N:3]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(C)C>[Cl:10][C:5]1[N:6]=[C:7]([CH:8]=[N:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:2]([NH2:1])=[N:3][C:4]=1[S:11][CH3:12]

Participants

4

Reactant 2

HCID 7504Benzylamine2×HCID 134721362-Amino-5-chloro-3-formyl-6-(methylthio)pyrazine

Product 1

HCID 204032315-Chloro-3-[(benzylimino)methyl]-6-(methylthio)pyrazineamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

In 2 ml of heated isopropanol there was dissolved 2-amino-5-chloro-3-formyl-6-(methylthio)pyrazine (60 mg; 0.3 mMol) prepared in Step A above. Benzylamine (35 mg; 0.33 mMol) was then added, and the reaction mixture was heated for 2 minutes on a steam bath, and then allowed to cool to room temperature. The reaction mixture was redissolved in 5 ml of isopropanol, a 20% excess of benzylamine was added, and stirring was continued overnight at room temperature. Product precipitated, was filtered and dried (38 mg).

Workup

  1. customprepared in Step A above
  2. temperaturethe reaction mixture was heated for 2 minutes on a steam bath
  3. customProduct precipitated
  4. filtrationwas filtered
  5. customdried (38 mg)

Sources & evidence

ORD record
ord-fb4c07b2df3448339f727d3933cc9f70
Source dataset
uspto-grants-1985_03
Patent number
US04507299

Reaction notes

Loading…