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

HRID 1817149Notes

Reaction equation

HRID 1817149 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-72aa06987f2b428ca5bc3609a46a03b4
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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