Sodium Hydroxide → HCID 178524688, compound

HRID 1026888Notes

Reaction equation

HRID 1026888 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([O:14]CC)=[O:13])[CH:8]=[N:7][C:6]=12.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[N:7][C:6]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469456HCID 178469456, compound

Product 1

HCID 178524688HCID 178524688, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-bromo-7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (Journal of Medicinal Chemistry, vol. 25, p. 235, 1982) (11.0 g, 38.5 mmol) was dissolved in ethanol (134 mL), 2 mol/L aqueous sodium hydroxide solution (134 mL, 269 mmol) was added, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was cooled to room temperature, and ethanol was evaporated under reduced pressure. 2 mol/L Hydrochloric acid (140 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. The precipitate was collected by filtration, and washed with water (100 mL) and 2-propanol (50 mL) to give the title compound (9.9 g, 99%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customethanol was evaporated under reduced pressure
  3. addition2 mol/L Hydrochloric acid (140 mL) was added under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 30 min
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water (100 mL) and 2-propanol (50 mL)

Sources & evidence

ORD record
ord-84dd34bdb76e4046937cdae061b624aa
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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