Hydrochloric Acid → HCID 12766252, compound

HRID 1278205Notes

Reaction equation

HRID 1278205 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([O:18]CC)=[O:17])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1.[OH-].[K+].Cl>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11196438ETHYL 7-(PYRIDIN-3-YL)PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE

Product 1

HCID 12766252HCID 12766252, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 0.10 mole of ethyl 7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate and 0.50 mole of potassium hydroxide in 50 ml. of ethanol-water (9:1) is heated at reflux temperature for 4 hours. The mixture is brought to pH 7 with concentrated hydrochloric acid, concentrated and filtered to give 7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. The preceding product in tetrahydrofuran is added dropwise to a solution of 0.2 mole of diborane in tetrahydrofuran chilled in an ice bath. The mixture is stirred for one hour and the bath removed. After standing 16 hours at room temperature the mixture is poured onto ice to give the product of the example.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. concentrationconcentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-87c4bc5e21b949faaee092b0340ba010
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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