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

HRID 31867
Notes
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Reaction equation

HRID 31867 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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-30af0f4e787a4f128d28b100741a27a8
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425557B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes