Lithium Hydroxide → 2-aminopyrimidine-5-carboxylic Acid

HRID 1259486Notes

Reaction equation

HRID 1259486 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10]C)=[O:9])=[CH:4][N:3]=1.[OH-].[Li+]>CO.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 9793866Methyl 2-aminopyrimidine-5-carboxylate

Product 1

HCID 70203672-aminopyrimidine-5-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-aminopyrimidine-5-carboxylate (300 mg, 2.0 mmol) was diluted in methanol (5 mL) containing a few drops of water. Lithium hydroxide (122 mg, 5.1 mmol) was added, and the reaction mixture was stirred at 60° C. overnight. The mixture was concentrated under reduced pressure, then diluted in water and adjusted to pH 4 with 1 M HCl. 2-Aminopyrimidine-5-carboxylic acid precipitated as a white solid, which was isolated by vacuum filtration (244 mg, 90%): 1H NMR (DMSO-d6) δ: 12.73 (1H, br s), 8.63 (2H, s), 7.44 (2H, br s).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted in water
  3. custom2-Aminopyrimidine-5-carboxylic acid precipitated as a white solid
  4. customwhich was isolated by vacuum filtration (244 mg, 90%)

Sources & evidence

ORD record
ord-bdc6f0c42e774fc7bff59ebd795fa7a1
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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