Hydrochloric Acid → HCID 58465053, compound

HRID 2089429Notes

Reaction equation

HRID 2089429 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]CC)=[O:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.O.[OH-].[Li+].Cl>C1COCC1>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 12258910Ethyl 5-amino-2-chloropyrimidine-4-carboxylate

Product 1

HCID 58465053HCID 58465053, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-amino-2-chloropyrimidine-4-carboxylate (0.90 g, 4.0 mmol) was dissolved in THF (22 mL). To it water (8 mL) and 1M lithium hydroxide (11 mL, 11 mmol) were added and the mixture was stirred at room temperature for 6 h. The reaction was then acidified to pH6 with 6N HCl (1.15 mL) and concentrated in vacuo to remove organic solvent. The solid was collected by filtration and washed with water to give 5-amino-2-chloropyrimidine-4-carboxylic acid as a yellow solid (434 mg, 60%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove organic solvent
  3. filtrationThe solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-06ee66782d7b4d2c8da7f90cf6422373
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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