Hydrochloric Acid → HCID 58465053, compound

HRID 69937Notes

Reaction equation

HRID 69937 reaction equation
[Li+].[OH-].[NH2:3][C:4]1[C:5]([C:11]([O:13]CC)=[O:12])=[N:6][C:7]([Cl:10])=[N:8][CH:9]=1.Cl>O.C1COCC1>[NH2:3][C:4]1[C:5]([C:11]([OH:13])=[O:12])=[N:6][C:7]([Cl:10])=[N:8][CH:9]=1

Participants

6

Reactant 3

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

Product 1

HCID 58465053HCID 58465053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0.5 M aqueous solution of LiOH (1.5 eq) was added to a stirring mixture of ethyl 5-amino-2-chloropyrimidine-4-carboxylate (1 eq) in H2O (0.1 M) and THF (0.1M). The reaction was maintained for 2 h at rt. 1.0 N HCl was added and the crude mixture was concentrated in vacuo to remove residual THF. The resulting solids were collected on a paper lined Buchner funnel and dried for 16 h under vacuum to give 5-amino-2-chloropyrimidine-4-carboxylic acid. LC/MS (m/z): 174.0 (MH+). HPLC: Rt: 1.148 min.

Workup

  1. concentrationthe crude mixture was concentrated in vacuo
  2. customto remove residual THF
  3. customThe resulting solids were collected on a paper
  4. customdried for 16 h under vacuum

Sources & evidence

ORD record
ord-3628fbeb12f949df9f2096812980f612
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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