Ethanol → HCID 70979820, compound

HRID 1403219Notes

Reaction equation

HRID 1403219 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[CH3:20])=[C:10]([C:21]([O:23]CC)=[O:22])[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]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 70979645HCID 70979645, compound

Product 1

HCID 70979820HCID 70979820, compoundYield 99.9%

Conditions

Temperature
5 °C

Procedure

Ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxylate (1.0 g, 2.80 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 2 N HCl was added, under agitation. The resultant precipitate was collected by filtration to give the title compound (0.92 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 2 N HCl was added, under agitation
  7. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-d5332b289e0f4aa7a8483cd3e67ab3b9
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…