2-Amino-5,6-dichloro-3-(1-hydroxyethyl)pyrazine → 1-(3-Amino-5,6-dichloropyrazin-2-yl)ethanone

HRID 1981159Notes

Reaction equation

HRID 1981159 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([OH:10])[CH3:9])=[N:6][C:5]([Cl:11])=[C:4]([Cl:12])[N:3]=1>CC(C)=O.[O-2].[O-2].[Mn+4]>[C:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([Cl:12])=[C:5]([Cl:11])[N:6]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 1

HCID 203998652-Amino-5,6-dichloro-3-(1-hydroxyethyl)pyrazine

Product 1

HCID 203998601-(3-Amino-5,6-dichloropyrazin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

In 6 ml of acetone there was dissolved 90 mg of 2-amino-5,6-dichloro-3-(1-hydroxyethyl)pyrazine prepared in Step A above, after which there was added 360 mg of manganese dioxide, and the reaction mixture was stirred for 3 days at room temperature. The manganese dioxide was filtered off, and the precipitate washed three times with acetone, and then filtered. The filtrate was concentrated under vacuum and passed through a silica gel column, then eluted first with hexane, followed by 10% dichloromethane in hexane, with product in the first three fractions (53 mg).

Workup

  1. filtrationThe manganese dioxide was filtered off
  2. washthe precipitate washed three times with acetone
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum
  5. washeluted first with hexane

Sources & evidence

ORD record
ord-02f1dd8c79604e7ab433fb06145d14a0
Source dataset
uspto-grants-1985_04
Patent number
US04512991

Reaction notes

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