4-Aminophenol → HCID 18452583, compound

HRID 1271037Notes

Reaction equation

HRID 1271037 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[CH:4][N:3]=1.[OH:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C(O)C>[ClH:1].[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]#[C:8][C:7]2[C:2]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([OH:17])=[CH:19][CH:20]=3)=[N:3][CH:4]=[N:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 184525694-Chloro-5-[(4-chlorophenyl)ethynyl]pyrimidine

Product 1

HCID 18452583HCID 18452583, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.28 g of 4-chloro-5-(4-Chlorophenylethynyl)pyrimidine, 10 mL of ethanol and 0.14 g of 4-hydroxyaniline was stirred at room temperature for 18 hours. The black mixture was evaporated in vacuo and the residue was triturated with dichloromethane, ethylacetate and acetonitrile. The combined organic extracts were absorbed on silica gel and evaporated in vacuo. The powder was added to a column of silica gel equilibrated in dichloromethane and eluted with the same solvent. The column was eluted with ethyl acetate and then 10% methanol in dichloromethane. These eluates on evaporation produced 100 mg of the 5-(4-chlorophenylethynyl)-4-(4-hydroxyanilino)pyrimidine hydrochloride as a muddy yellow powder.

Workup

  1. customThe black mixture was evaporated in vacuo
  2. customthe residue was triturated with dichloromethane, ethylacetate and acetonitrile
  3. customThe combined organic extracts were absorbed on silica gel
  4. customevaporated in vacuo
  5. additionThe powder was added to a column of silica gel
  6. washeluted with the same solvent
  7. washThe column was eluted with ethyl acetate
  8. customThese eluates on evaporation

Sources & evidence

ORD record
ord-c27e4aaad69e476e981dc0c27e7b57f2
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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