Hydrazine hydrate (1:1) → 3-Amino-6-(dimethoxymethyl)pyrazine-2-carbonitrile

HRID 4443Notes

Reaction equation

HRID 4443 reaction equation
O.NN.[C:4]([C:6]1[C:7]([N:17]2C(=O)C3=CC=CC=C3C2=O)=[N:8][CH:9]=[C:10]([CH:12]([O:15][CH3:16])[O:13][CH3:14])[N:11]=1)#[N:5]>CO>[NH2:17][C:7]1[C:6]([C:4]#[N:5])=[N:11][C:10]([CH:12]([O:15][CH3:16])[O:13][CH3:14])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 136047823-Cyano-5-dimethoxymethyl-2-phthalimidopyrazine

Product 1

HCID 126251323-Amino-6-(dimethoxymethyl)pyrazine-2-carbonitrileYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g of hydrazine hydrate were added dropwise to a suspension of 2 g of 3-cyano-5-dimethoxymethyl-2-phthalimidopyrazine in 40 ml of absolute methanol at 40° C. Immediately after the addition, the solution became clear, and crystals were precipitated after a few minutes. Chromatography over silica gel gave 0.9 g (75%) of 2-amino-3-cyano-5-dimethoxymethylpyrazine. 1H-NMR (270 MHz, DMSO-d6): δ3.3 (s, 6H), 5.0 (s, 1H), 8.35 (s, 1H).

Workup

  1. additionImmediately after the addition
  2. customcrystals were precipitated after a few minutes

Sources & evidence

ORD record
ord-8989c551d2d14ccc86118bea21ea1108
Source dataset
uspto-grants-1988_02
Patent number
US04725689

Reaction notes

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