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Hydrochloric Acid → 2-((4-Cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid

HRID 2284654
Notes
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Reaction equation

HRID 2284654 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([O:22]CC)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2].Cl>C(O)C.O1CCCC1.[OH-].[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([OH:22])=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 90052034Ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate

Product 1

HCID 900520362-((4-Cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acidYield 89.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent
HCID 14798
Sodium Hydroxide
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (C4, 0.90 g) in ethanol (10 mL) and tetrahydrofuran (5 mL), 2.0 mol/L aqueous sodium hydroxide (2.8 mL) was added at room temperature, and the mixture was stirred at 50° C. for 5 hours. The reaction mixture was cooled to room temperature, and then 1.0 mol/L aqueous hydrochloric acid was added to the reaction mixture until the mixture became acidic. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid (C5, 738 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-31d98e3552374cffaf7a3e3294ebc1c7
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes