Ethanol → 5-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-ethyl-1H-pyrrole-3-carboxylic acid

HRID 1619084Notes

Reaction equation

HRID 1619084 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)=[CH:20][C:19]=3[O:31][CH3:32])[N:12]=2)[N:8]([CH3:33])[CH:7]=1)=[O:5])C.[OH-].[K+].[CH2:36](O)C>>[CH3:32][O:31][C:19]1[CH:20]=[C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)[CH:22]=[CH:23][C:18]=1[NH:17][C:13]1[N:12]=[C:11]([C:9]2[N:8]([CH2:33][CH3:36])[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:10]=2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 666782985-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 666874105-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-ethyl-1H-pyrrole-3-carboxylic acidYield 100%

Procedure

5-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (160 mg, 0.355 mmol) was suspended in ethanol (13 mL) and treated with a 1.5 M solution of potassium hydroxide in ethanol (2.4 mL, 10 eq.) at reflux temperature for 3 hour. Solvent was evaporated to dryness and the residue dissolved in water. After treatment with acetic acid and the resulting precipitate was collected by filtration to give the title compound (150 mg, 100% yield) as a white solid.

Workup

  1. temperatureat reflux temperature for 3 hour
  2. customSolvent was evaporated to dryness
  3. dissolutionthe residue dissolved in water
  4. filtrationAfter treatment with acetic acid and the resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-26d854af01a04255812725994618ba40
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

Loading…