Water → (2-Aminoethyl)[4-(2,4-dichlorophenyl)-5-imidazolylpyrimidin-2-yl]methylamine

HRID 1823540Notes

Reaction equation

HRID 1823540 reaction equation
N1C=CC=NC=1.[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[C:15]1[C:20]([C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)=[CH:19][N:18]=[C:17]([CH2:26][NH:27][CH2:28][CH2:29][NH:30]C(=O)C(F)(F)F)[N:16]=1.[OH-].[K+].O>CO>[NH2:30][CH2:29][CH2:28][NH:27][CH2:26][C:17]1[N:16]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=2[Cl:7])[C:20]([C:21]2[NH:25][CH:24]=[CH:23][N:22]=2)=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9260PyrimidineHCID 14797Potassium HydroxideHCID 86586216N-(2-{[4-(2,4-dichlorophenyl)-5-imidazolyl-pyrimidin-2-yl]methylamino}ethyl)-2,2,2-trifluoroacetamide

Product 1

HCID 54421065(2-Aminoethyl)[4-(2,4-dichlorophenyl)-5-imidazolylpyrimidin-2-yl]methylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The aforementioned pyrimidine, N-(2-{[4-(2,4-dichlorophenyl)-5-imidazol-2-ylpyrimidin-2-yl]methylamino}ethyl)-2,2,2-trifluoroacetamide (114 mg, 0.25 mmol) was dissolved in 2 mL methanol and potassium hydroxide (40 mg, 1 mmol) added. This suspension was stirred at room temperature for 1 hour. Water was added, and the solution extracted with methylene chloride. The aqueous layer was thoroughly extracted with methylene chloride and the organic layers washed with brine, dried and concentrated to give the deprotected primary amine, (2-aminoethyl)[4-(2,4-dichlorophenyl)-5-imidazol-2-ylpyrimidin-2-yl]methylamine in quantitative yield.

Workup

  1. extractionthe solution extracted with methylene chloride
  2. extractionThe aqueous layer was thoroughly extracted with methylene chloride
  3. washthe organic layers washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a392c481af7b490a8f9ec17aaf31aa31
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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