Hydrochloric Acid → 3-Amino-5-methylpyrazine-2-carboxylic acid

HRID 81490Notes

Reaction equation

HRID 81490 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6]([OH:13])=NC(O)=[N:9]2)=[N:4][CH:3]=1.[OH-:14].[Na+].Cl>O>[NH2:9][C:10]1[C:5]([C:6]([OH:13])=[O:14])=[N:4][CH:3]=[C:2]([CH3:1])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178430068HCID 178430068, compound

Product 1

HCID 2792333-Amino-5-methylpyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

7-Methyl-pteridine-2,4-diol (prepared by the procedure of ‘Synthesis of 2,6-Disubstituted pyrazines and Related Derivates.’, Sharefkin, D. M. J. Am. Chem. Soc., 1959, 345) (4 g, 22.5 mmol) is suspended in a solution of NaOH (2.17 g, 53 mmol) in H2O (20 ml), in an autoclave, and the mixture is heated to 150° C. for 3 days. The reaction mixture is cooled to room temperature and the pH is adjusted to 2.5 by the slow addition of 6M HCl (98 ml). The resulting suspension is cooled in a fridge for 1.5 hours, and the solid is then collected by filtration, washed with cold H2O, and MeOH, and dried in vacuo to yield 3-amino-5-methyl-pyrazin-2-carboxylic acid as a beige solid. [M+H]+ 154

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. temperatureThe resulting suspension is cooled in a fridge for 1.5 hours
  3. filtrationthe solid is then collected by filtration
  4. washwashed with cold H2O, and MeOH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-20f096293c004307bff111bd3ab5d3c2
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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