Potassium Hydroxide → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid

HRID 225259Notes

Reaction equation

HRID 225259 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([O:20]CC)=[O:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.[OH-].[K+]>C(O)C.O>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([OH:20])=[O:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23329853Ethyl 4-(alpha,alpha,alpha-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylate

Product 1

HCID 233298734-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 2 g. of ethyl 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylate, 2 g. of potassium hydroxide and 50 ml. of ethanol:water (9:1) is refluxed for 4 hours. The mixture is concentrated, diluted with water and the solid 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid isolated. The preceding compound is heated neat at 190° C. to give the product of the example.

Workup

  1. additionA mixture of 2 g
  2. concentrationThe mixture is concentrated
  3. additiondiluted with water

Sources & evidence

ORD record
ord-71604b39f317431ba236a97228424478
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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