Hydrochloric Acid → HCID 58465053, compound

HRID 1185386Notes

Reaction equation

HRID 1185386 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-13a4a9715f394b05b7cc6978fa76e4e1
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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