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N,N-Diethylaniline → HCID 21475298, compound

HRID 2294532
Notes
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Reaction equation

HRID 2294532 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[CH:4][CH:3]=1.Cl.[C:12]([C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])[NH2:19])([CH3:15])([CH3:14])[CH3:13].CCN(C1C=CC=CC=1)CC>C1(C)C=CC=CC=1>[C:12]([C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[CH:4][CH:3]=2)[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:15])([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 122015644-Amino-2,6-di-tert-butylphenol hydrochlorideHCID 122816477-Chloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 21475298HCID 21475298, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 7-chloropyrazolo[1,5-a]pyrimidine (1.0 g), 3,5-di-t-butyl-4-hydroxyaniline hydrochloride (1.8 g) and diethylaniline (2.3 ml) in toluene (50 ml) is heated at 120° C. for 30 minutes. After cooling, the solvent is distilled off, and the residue is purified by silica gel column chromatography (solvent; CHCl3) to give 7-(3,5-di-t-butyl-4-hydroxyphenyl)aminopyrazolo[1,5-a]pyrimidine (890 mg) as colorless crystal.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent is distilled off
  3. customthe residue is purified by silica gel column chromatography (solvent; CHCl3)

Sources & evidence

ORD record
ord-87849fe6b5e049e0938ca9418af39b88
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05688949

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes