Methanol → N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine

HRID 1785325Notes

Reaction equation

HRID 1785325 reaction equation
[Br:1][C:2]1[C:3]([NH:22][CH2:23][CH2:24][C:25]2[NH:26][CH:27]=[N:28][CH:29]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)C(F)(F)F)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.CO.O.[Li+].[OH-]>C1COCC1>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:22][CH2:23][CH2:24][C:25]3[NH:26][CH:27]=[N:28][CH:29]=3)[C:2]([Br:1])=[CH:7][N:6]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57593354HCID 57593354, compound

Product 1

HCID 57593472N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamineYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl)-trifluoro acetamide (1 g, 1.9 mmole) was dissolved in THF (10 ml), MeOH (10 ml) and water (5 ml) and LiOH (455 mg) was added in one portion at room temperature. The reaction mixture was stirred at room temperature for two days, the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate and water and extracted with ethyl acetate (3×). The combined organic layers were combined and dried over magnesium sulfate. After evaporation of the solvent one obtains 350 mg of N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine. ESI-MS: 375.

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionwater and extracted with ethyl acetate (3×)
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent one

Sources & evidence

ORD record
ord-377186965de8430eb780d36727c57999
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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