Potassium Carbonate → 2-Amino-3-cyano-5-ethynylpyrazine

HRID 440901Notes

Reaction equation

HRID 440901 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:10]#[C:11][Si](C)(C)C)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:10]#[CH:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 153352712-Amino-3-cyano-5-(trimethylsilylethynyl)pyrazine

Product 1

HCID 153352732-Amino-3-cyano-5-ethynylpyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.3 grams (0.006 mole) of 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine and 0.9 gram (0.006 mole) of potassium carbonate in 50 mL of methanol is stirred at ambient temperature for one hour. The reaction mixture is then concentrated under reduced pressure to a residue. The residue is taken up in about 75 mL of water, and the solution is extracted with two 200 mL portions of ethyl acetate. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 2-amino-3-cyano-5-ethynylpyrazine. This reaction is repeated several times.

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure to a residue
  2. extractionthe solution is extracted with two 200 mL portions of ethyl acetate
  3. dry with materialThe combined extracts are dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-2870652595d84b51bcae25d82eabd9b5
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Reaction notes

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