Potassium Hydroxide → HCID 21471626, compound

HRID 2294946Notes

Reaction equation

HRID 2294946 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21471548Ethyl 2-tert-butoxycarbonylamino-5-pyrimidinecarboxylate

Product 1

HCID 21471626HCID 21471626, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 200 mg of ethyl 2-tert-butoxycarbonylamino-5-pyrimidinecarboxylate, 125 mg of potassium hydroxide and 15 mL of ethanol was heated to 70° C. for 3 h, cooled and concentrated under reduced pressure. The residue was dissolved in 50 mL of ice water, washed with 50 mL of ether, acidified to pH=3 with conc. HCl and extracted with 3×50 mL of chloroform. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Drying under vacuum gave 156 mg of 2-tert-butoxycarbonylamino-5-pyrimidinecarboxylic acid as a white solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 mL of ice water
  4. washwashed with 50 mL of ether
  5. extractionextracted with 3×50 mL of chloroform
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customDrying under vacuum

Sources & evidence

ORD record
ord-88c8fe8c6f724be8afdef73aa59895a5
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

Loading…