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Chloroform → N-(3-(methylamino)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 2284639
Notes
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Reaction equation

HRID 2284639 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20](C)[C:21](=O)C(F)(F)F)[CH:15]=2)=[O:12])=[CH:9][N:8]=[C:7]([NH:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[N:6]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CO.O>[CH3:21][NH:20][C:16]1[CH:15]=[C:14]([NH:13][C:11]([C:10]2[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][C:7]([NH:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=3)=[N:8][CH:9]=2)=[O:12])[CH:19]=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 900520024-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(3-(2,2,2-trifluoro-N-methylacetamido)phenyl)pyrimidine-5-carboxamide

Product 1

HCID 90052010N-(3-(methylamino)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamideYield 93.8%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent2×

Procedure

To a solution of 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(3-(2,2,2 -trifluoro-N-methylacetamido)phenyl)pyrimidine-5-carboxamide (A7, 186 mg) in methanol (4 mL) and water (2 mL), potassium carbonate (92 mg) was added at room temperature, and the mixture was stirred at the same temperature for 13 hours and 30 minutes. To the reaction mixture, water and chloroform were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain N-(3-(methylamino)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (A8, 141 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-515f098fd9e2459587ccf07c0bb9af20
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145415B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes