Triethylamine → Methyl 2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylate

HRID 16773

Reaction equation

HRID 16773 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CC(O)C>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 57440399Methyl 2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylateYield 34.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-chloropyrimidine-5-carboxylate (0.863 g, 5.0 mmol), N,N-diethylethanamine (0.697 ml, 5.00 mmol) and 1-methylpiperazine (0.565 ml, 5.09 mmol) were suspended in 2-propanol (10.00 ml) and sealed into a microwave tube. The reaction was heated to 100° C. for 10 mins in the microwave reactor and cooled to room temperature. The precipitate was collected by filtration, washed with EtOH (5 mL) and dried under vacuum to afford methyl 2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylate (0.405 g, 34.3%) as a white solid, which was used without further purification.

Workup

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with EtOH (5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3d8faf17cfac41e6a7efe3ee879d0db9
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Linked notes

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