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Diisopropylethylamine → HCID 15512221, compound

HRID 635211
Notes
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Reaction equation

HRID 635211 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15](Cl)[N:14]=3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Br:22][C:23]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:24]=1[NH2:25].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>C(O)CO>[Br:22][C:23]1[CH:29]=[C:28]([CH:30]([CH3:31])[CH3:32])[CH:27]=[CH:26][C:24]=1[NH:25][C:15]1[N:14]=[C:13]([N:10]2[CH2:11][CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[CH:18]=[C:17]([CH3:19])[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 15512220HCID 15512220, compoundHCID 212582072-Bromo-4-isopropylaniline hydrochloride

Product 1

HCID 15512221HCID 15512221, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 174
Ethylene Glycol
Solvent

Procedure

4-(4-Phenyl-1,2,3,6-tetrahydropyridin-1-yl)-2-chloro-6-methylpyrimidine (466 mg), 408 mg of 2-bromo-4-isopropylaniline hydrochloride and 232 mg of diisopropylethylamine were heated in 5 ml of ethylene glycol under reflux for 1 hour. The reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The desiccant was filtered off, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=6/1) to give 458 mg of 2-[N-(2-bromo-4-isopropylphenyl)amino]-4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-6-methylpyrimidine as an amorphous substance.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-1b6ea8cf99c54d7d8e87e4dd255c3186
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06187781B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes