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Pyridine → 4-[4-(4-Nitrophenyl)-1-piperazinyl]-2,6-di(1-pyrrolidinyl)pyrimidine

HRID 2104302
Notes
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Reaction equation

HRID 2104302 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:3]=1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1)([O-:20])=[O:19].N1C=CC=CC=1>O>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([C:2]3[CH:7]=[C:6]([N:8]4[CH2:12][CH2:11][CH2:10][CH2:9]4)[N:5]=[C:4]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)[N:3]=3)[CH2:29][CH2:28]2)=[CH:25][CH:26]=1)([O-:20])=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 804471-(4-Nitrophenyl)piperazineHCID 7036994-Chloro-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 187658234-[4-(4-Nitrophenyl)-1-piperazinyl]-2,6-di(1-pyrrolidinyl)pyrimidineYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2.52 g (10 mmol) of 4-chloro-2,6-di-pyrrolidin-1-yl-pyrimidine (J. Med. Chem. (1990) 33 (4), 1145-1151) and 2.07 g (10 mmol) of 4-nitrophenylpiperazine are dissolved in a 250 ml flask containing 20 ml of anhydrous pyridine, under an argon atmosphere. The reaction mixture is heated at 100° C. for 48 hours. After cooling down, the contents of the flask are poured into 250 ml of water and the product is extracted using twice 50 ml of CH2Cl2. The organic phase is then washed with 50 ml of brine, dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is purified on a silica column (eluent: Heptane/AcOEt: 2/1). An orange solid is obtained with a yield of 49%. Melting point: 200-201° C.

Workup

  1. temperatureAfter cooling down
  2. extractionthe product is extracted
  3. washThe organic phase is then washed with 50 ml of brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified on a silica column (eluent: Heptane/AcOEt: 2/1)
  8. customAn orange solid is obtained with a yield of 49%

Sources & evidence

ORD record
ord-8ca026f036f1410a98fd24d59bb4701c
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576241B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes