HCID 20463835, compound → 5,6-Dichloro-3-[(2-hydroxyethyl)amino]pyrazine-2-carbaldehyde

HRID 325608Notes

Reaction equation

HRID 325608 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:13][OH:14])[C:5]([NH:9][CH2:10][CH2:11][OH:12])=[N:6][C:7]=1[Cl:8]>CC(C)=O.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:3]=[C:4]([CH:13]=[O:14])[C:5]([NH:9][CH2:10][CH2:11][OH:12])=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 20463835HCID 20463835, compound

Product 1

HCID 204638365,6-Dichloro-3-[(2-hydroxyethyl)amino]pyrazine-2-carbaldehydeYield 71.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 180AcetoneSolvent

Procedure

A mixture of 5,6-dichloro-3-hydroxymethyl-2-(2-hydroxyethyl)aminopyrazine (38 mg; 0.00016 Mol), prepared as in Step C above, and manganese dioxide (12 mg) was stirred at room temperature for 2.5 hours. Another 24 mg of manganese dioxide was added and stirring was continued for another 5 hours. The manganese dioxide was filtered off, and the precipitate was washed well with acetone. The crude reaction mixture dissolved in 1.5 l of acetone and 36 mg of manganese dioxide was added, followed by stirring at room temperature for 3.5 hours. The manganese dioxide was filtered off, and the precipitate was washed twice with acetone. The filtrate was concentrated under vacuum and passed through a silica gel column, eluting with dichloromethane, then 1:1 ethyl acetate/dichloromethane, to give the title compound (27 mg). Elemental Analysis for C7H7O2N3Cl2 :

Workup

  1. stirringstirring
  2. waitwas continued for another 5 hours
  3. filtrationThe manganese dioxide was filtered off
  4. washthe precipitate was washed well with acetone
  5. customThe crude reaction mixture
  6. stirringby stirring at room temperature for 3.5 hours
  7. filtrationThe manganese dioxide was filtered off
  8. washthe precipitate was washed twice with acetone
  9. concentrationThe filtrate was concentrated under vacuum
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-a665aae9153149b080c5fd4e9e4a120a
Source dataset
uspto-grants-1984_04
Patent number
US04442097

Reaction notes

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