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1-Piperazinecarboxylic acid, ethyl ester → 4-(Ethoxycarbonyl)-1-(5-ethoxy-4-pyrimidinyl)piperazine

HRID 1463351
Notes
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Reaction equation

HRID 1463351 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][N:5]=[CH:4][N:3]=1.[N:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:20]([O:19][C:17]([N:11]1[CH2:12][CH2:13][N:14]([C:2]2[C:7]([O:8][CH2:9][CH3:10])=[CH:6][N:5]=[CH:4][N:3]=2)[CH2:15][CH2:16]1)=[O:18])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 19003014HCID 19003014, compound

Product 1

HCID 199216314-(Ethoxycarbonyl)-1-(5-ethoxy-4-pyrimidinyl)piperazineYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-chloro-5-ethoxypyrimidine (1.98 g, 12.5 mmol), ethyl 1-piperazinecarboxylate (5.93 g, 37.5 mmol) and micropulverized K2CO3 (5.18 g, 37.5 mmol) was heated at reflux in CH3CN (75 mL) for 4 h. Upon cooling to 23° C., the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with water (5 mL). The organic phase was dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure. Silica gel chromatography (CH2Cl2 /MeOH;98:2) of the concentrate yielded product (2.29 g, 65%).

Workup

  1. temperaturewas heated
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water (5 mL)
  5. dry with materialThe organic phase was dried with anhydrous K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-031a8e4f5b9443339cccaa8e3398a4b9
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05300506

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes