Hydrochloric Acid → 6-Chloro-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid

HRID 2368345Notes

Reaction equation

HRID 2368345 reaction equation
C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:10][CH:9]=[C:8]([Cl:19])[N:7]=1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1.C(O)C>[Cl:19][C:8]1[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]([NH:12][C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 866601932-Pyridinecarboxylic acid, 6-chloro-3-(5-pyrimidinylamino)-, ethyl ester

Product 1

HCID 866601946-Chloro-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 6-chloro-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (98 mg, 0.35 mmol) in THF (1 ml) and ethanol (0.5 ml) was cooled to 0° C. and treated with 1M LiOH (0.7 ml, 0.7 mmol). The ice bath was removed and the reaction mixture was stirred at rt. for 2 h. 1M HCl (0.7 ml, 0.7 mmol) was added and stirring was continued until a precipitate was forming. The reaction mixture was sucked off and the product was obtained upon drying of the precipitate as yellow solid (60 mg, 67%).

Workup

  1. customThe ice bath was removed
  2. stirringstirring
  3. customwas forming
  4. customthe product was obtained
  5. dry with materialupon drying of the precipitate as yellow solid (60 mg, 67%)

Sources & evidence

ORD record
ord-458402e3351d4a09b22a7339de391fc2
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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