Methyl 3-aminopyrazinecarboxylate → 3-Aminopyrazine-2-carbaldehyde

HRID 2373164Notes

Reaction equation

HRID 2373164 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[NH2:11][C:10]1[C:5]([CH:3]=[O:2])=[N:6][CH:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 72669Methyl 3-aminopyrazinecarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 152749313-Aminopyrazine-2-carbaldehydeYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl-3-aminopyrazine-2-carboxylate (11 g) was dissolved in THF and cooled to −78° C. Diisobutylaluminum hydride (1M in hexanes, 250 mL) was added, and the reaction stirred at −78° C. for 4 hours. The reaction was then warmed to 0° C. for one hour before being quenched slowly by addition of 1M hydrochloric acid. Ethyl acetate was added and the layers separated. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was triturated in hexanes to afford title compound (3.0 g, 34%).

Workup

  1. temperatureThe reaction was then warmed to 0° C. for one hour
  2. custombefore being quenched slowly by addition of 1M hydrochloric acid
  3. additionEthyl acetate was added
  4. customthe layers separated
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in hexanes

Sources & evidence

ORD record
ord-e86c4a5f58684bc281ea0e8a2329626f
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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