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Ammonium formate → 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(pyrrolidin-3-yl)pyrimidine-5-carboxamide

HRID 2284700
Notes
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Reaction equation

HRID 2284700 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]2[C:21]([NH:35][CH2:36][CH2:37][CH3:38])=[N:22][C:23]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[N:24][CH:25]=2)=[O:19])[CH2:13]1)C1C=CC=CC=1>CO.[C].[Pd]>[CH2:36]([NH:35][C:21]1[C:20]([C:18]([NH:17][CH:14]2[CH2:15][CH2:16][NH:12][CH2:13]2)=[O:19])=[CH:25][N:24]=[C:23]([NH:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)[N:22]=1)[CH2:37][CH3:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90051742N-(1-benzylpyrrolidin-3-yl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide

Product 1

HCID 900517414-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(pyrrolidin-3-yl)pyrimidine-5-carboxamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst
HCID 887
Methanol
Solvent
3×

Procedure

To a suspension of 10% palladium-carbon (12 mg) in methanol (1 mL), a solution of ammonium formate (64 mg) and N-(1-benzylpyrrolidin-3-yl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (E9, 117 mg) in methanol (4 mL) was added at room temperature, and the mixture was stirred for 5 hours and 30 minutes under reflux by heating. The reaction mixture was cooled to room temperature, and then methanol was added to the mixture. The insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography to obtain 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)-N-(pyrrolidin-3-yl)pyrimidine-5-carboxamide (E10, 85 mg).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. customThe insoluble matter was removed by filtration through Cerite
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-92cc3c6f3efc45ba99dedde152812f74
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