Ethanol → HCID 70979618, compound

HRID 924679Notes

Reaction equation

HRID 924679 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=3[Cl:23])=[C:10]([C:24]([O:26]CC)=[O:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[K+].CCO>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[CH:15][C:14]=3[Cl:23])=[C:10]([C:24]([OH:26])=[O:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 70979619HCID 70979619, compound

Product 1

HCID 70979618HCID 70979618, compoundYield 95%

Conditions

Temperature
5 °C

Procedure

Ethyl 5-(2-aminopyrimidin-4-yl)-2-[2-chloro-5-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate (1.0 g, 2.43 mmol) was treated with a 1.5 M solution of potassium hydroxide in 95% EtOH (32.4 mL, 20 eq) under reflux for 20 h. After cooling, the residue was concentrated, dissolved in water and washed with DCM. To the aqueous phase cooled to 5° C., a solution of HCl 2 N was added, under agitation. The resulting precipitate was collected by filtration to give the title compound (0.88 g, 95%).

Workup

  1. temperatureunder reflux for 20 h
  2. temperatureAfter cooling
  3. concentrationthe residue was concentrated
  4. dissolutiondissolved in water
  5. washwashed with DCM
  6. additiona solution of HCl 2 N was added, under agitation
  7. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-19f192d43ba6439da68b44be079817a5
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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