1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-(5-ethoxy-4-pyrimidinyl)-1-piperazinecarboxylate

HRID 1647803Notes

Reaction equation

HRID 1647803 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]

Participants

5

Reactant 3

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

Product 1

HCID 19921631Ethyl 4-(5-ethoxy-4-pyrimidinyl)-1-piperazinecarboxylateYield 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. customwas 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-be9cc9874ef24d2396173375641611f8
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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