Ethyl Acetate → N-(3-aminopropyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 2284642Notes

Reaction equation

HRID 2284642 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([NH:13][CH2:14][CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)=[O:12])=[CH:9][N:8]=[C:7]([NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[N:6]=1)[CH2:2][CH3:3].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[NH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]([C:10]1[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][C:7]([NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[N:8][CH:9]=1)=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 90052194Tert-butyl (3-(4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamido)propyl)carbamate

Product 1

HCID 90052165N-(3-aminopropyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamideYield 64.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl (3-(4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamido)propyl)carbamate (B3, 281 mg) in chloroform (2 mL), trifluoroacetic acid (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted three times with chloroform. The organic layer and the extracts were combined, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 85 to 70% ethyl acetate in methanol) to obtain N-(3-aminopropyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (B4, 142 mg) as white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted three times with chloroform
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 85 to 70% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-7b38db6312ca439b8c596eaa46ffcb85
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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