Acetic Anhydride → HCID 10608334, compound

HRID 326827Notes

Reaction equation

HRID 326827 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[C:12]([O:15][C:16](=O)[CH3:17])(=O)C>>[CH3:12][O:15][CH2:16][C:17]1[N:10]([CH3:11])[C:8](=[O:9])[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[N:1]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 108207483-Amino-N-methylpyrazine-2-carboxamide

Product 1

HCID 10608334HCID 10608334, compound

Procedure

A mixture of 7.8 g (0.0513 mole) of 3-amino-N-methyl-2-pyrazinecarboxamide [prepared according to W. F. Keir et al., J. Chem. Soc., Perkin Trans 1, 1978, 1002], 39.4 g (0.205 mole) of triethyl orthomethoxyacetate and 45.3 ml of acetic anhydride is refluxed under a nitrogen atmosphere for 3 hours. The temperature of this reflux falls with the passage of time from 114° to 90° C. and then remains constant at the latter temperature. After cooling, the reaction mixture is concentrated to dryness under reduced pressure. The residue obtained is purified by chromatography on a silica column (eluent: chloroform/methanol, 95:5 and then 90:10), and is then recrystallized from ethyl acetate. Yld: 5.0 g (47%), m.p. 130.5°-132.5° C.

Workup

  1. temperatureis refluxed under a nitrogen atmosphere for 3 hours
  2. customfalls with the passage of time from 114° to 90° C.
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column (eluent
  7. customchloroform/methanol, 95:5 and then 90:10), and is then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-82bbcce980bd4e58a9926eaa9f81cb28
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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