Ethanol → HCID 71239580, compound

HRID 1403237Notes

Reaction equation

HRID 1403237 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]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH2:20][CH3:21])=[C:10]([C:22]([O:24]CC)=[O:23])[CH:9]=2)[C:5]([Br:27])=[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]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH2:20][CH3:21])=[C:10]([C:22]([OH:24])=[O:23])[CH:9]=2)[C:5]([Br:27])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 71239723HCID 71239723, compound

Product 1

HCID 71239580HCID 71239580, compoundYield 95%

Conditions

Temperature
5 °C

Procedure

Ethyl 5-(2-amino-5-bromopyrimidin-4-yl)-2-(5-chloro-2-ethylphenyl)-1H-pyrrole-3-carboxylate (400 mg, 0.89 mmol) was treated with a 1.5 M solution of potassium hydroxide in 95% EtOH (11.86 mL, 20 eq) under reflux overnight. After cooling, the residue was concentrated, dissolved in water and washed with DCM. To the aqueous phase cooled to 5° C., a solution of 2 N HCl was added, under agitation. The resultant precipitate was collected by filtration to give the title compound (356 mg, 95%).

Workup

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

Sources & evidence

ORD record
ord-ee5dc1d9bea3421e8cd42175b99c504c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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