Potassium Cyanide → alpha-Amino-5-pyrimidineacetonitrile

HRID 1681900Notes

Reaction equation

HRID 1681900 reaction equation
[C-:1]#[N:2].[K+].[Cl-].[NH4+:5].[N:6]1[CH:11]=[C:10]([CH:12]=O)[CH:9]=[N:8][CH:7]=1>O.CO>[NH2:5][CH:12]([C:10]1[CH:11]=[N:6][CH:7]=[N:8][CH:9]=1)[C:1]#[N:2]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 2761034Pyrimidine-5-carboxaldehyde

Product 1

HCID 20080448alpha-Amino-5-pyrimidineacetonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium cyanide (651 mg, 10 mmol) and ammonium chloride (588 mg, 11 mmol) are dissolved in water (2.6 mL) with stirring. Pyrimidine-5-carboxaldehyde (1.08 g, 10 mmol) in methanol (2.6 mL) is added to the clear solution rapidly, giving first a yellow, then a dark red solution, and mildly exothermic reaction. The water is evaporated after three hours stirring, and the reddish residue is chromatographed (silica, chloroform/methanol) to give a yellow solid 1.1 g (82%) identified as product ms m/z=134.

Workup

  1. customgiving first a yellow, then
  2. customa dark red solution, and mildly exothermic reaction
  3. customThe water is evaporated after three hours
  4. stirringstirring
  5. customthe reddish residue is chromatographed (silica, chloroform/methanol)

Sources & evidence

ORD record
ord-f1c71fa1a59d41c091146f9073a4d6e6
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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