Propargylamine → 6-Chloro-5-(2-propyn-1-ylamino)-2-pyrazinecarboxylic acid

HRID 1733467Notes

Reaction equation

HRID 1733467 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][C:14]#[CH:15]>O1CCOCC1>[Cl:8][C:7]1[C:2]([NH:12][CH2:13][C:14]#[CH:15])=[N:3][CH:4]=[C:5]([C:9]([OH:11])=[O:10])[N:6]=1

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 202996445,6-Dichloropyrazine-2-carboxylic acid

Product 1

HCID 202996246-Chloro-5-(2-propyn-1-ylamino)-2-pyrazinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,3-dichloropyrazine-5-carboxylic acid (19.3 g, 0.100 mole) and 3-amino-1-propyne (1.10 g, 0.20 mole) in 100 ml dioxane is refluxed for 24 hours, cooled and concentrated under vacuum. The residue is partitioned between aqueous sodium bicarbonate and chloroform and the aqueous extract neutralized with acetic acid to give a precipitate of 3-chloro-2-(2-propyn-1-ylamino)pyrazine-5-carboxylic acid.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. customThe residue is partitioned between aqueous sodium bicarbonate and chloroform
  5. extractionthe aqueous extract

Sources & evidence

ORD record
ord-21e9929954bc4d0b8f2691a5f480b50c
Source dataset
uspto-grants-1980_12
Patent number
US04242344

Reaction notes

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