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Diisopropylethylamine → (S)-4-{6-Chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin-4-yl}piperazin-2-one

HRID 1187671
Notes
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Reaction equation

HRID 1187671 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][C:20]1=[O:25].C(N(CC)C(C)C)(C)C>C(O)CCC.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=[C:2]([N:22]2[CH2:23][CH2:24][NH:19][C:20](=[O:25])[CH2:21]2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

Product 1

HCID 86659374(S)-4-{6-Chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin-4-yl}piperazin-2-oneYield 106.9%

Reagents, catalysts & solvents 2

HCID 2631-Butanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 150 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine and 58 mg of piperazin-2-one in 1.5 ml of 1-butanol was added 183 μl of N,N-diisopropylethylamine, and the mixture was stirred at 60° C. for 20 hours. The reaction solution was air-cooled to room temperature, and then diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 196 mg of the objective compound as white powder.

Workup

  1. temperatureThe reaction solution was air-cooled to room temperature
  2. washThe solution was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2f6b1219f29b41bc9d8f44c1091c5b7a
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673891B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes