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Diisopropylethylamine → HCID 21258204, compound

HRID 635218
Notes
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Reaction equation

HRID 635218 reaction equation
[C:1]1([C:7]2[CH2:12][N:11]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15](Cl)[N:14]=3)[CH2:10][CH2:9][CH:8]=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:11]2[CH2:12][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH2:9][CH2:10]2)[CH:18]=[C:17]([CH3:19])[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 21258202HCID 21258202, compoundHCID 212582072-Bromo-4-isopropylaniline hydrochloride

Product 1

HCID 21258204HCID 21258204, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 174
Ethylene Glycol
Solvent

Procedure

4-(5-Phenyl-1,2,3,6-tetrahydropyridin-1-yl)-2-chloro-6-methylpyrimidine (1.10 g), 2-bromo-4-isopropylaniline hydrochloride (0.97 g), and diisopropylethylamine (0.50 g) were heated at reflux in 5 ml of ethylene glycol for 1 hour. The reaction solution was poured into a saturated sodium hydrogencarbonate aqueous solution and extracted with ethyl acetate. The extract was washed with water and then with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to give 1.32 g of 2-[N-(2-bromo-4-isopropylphenyl)amino]-4-(5-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-6-methylpyrimidine as an amorphous substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialwith a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-fac391b0fad84f0ab30021cbf62918de
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