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Sodium Hydroxide → HCID 486392, Verbindung

HRID 1070950
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1070950
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[NH2:18][C:19]1[C:26]([CH3:27])=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1[CH3:28].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>C(Cl)Cl.O1CCOCC1.CN1CCCC1=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([NH:9][C:4]2[N:3]=[C:2]([NH:18][C:19]3[C:20]([CH3:28])=[CH:21][C:22]([C:23]#[N:24])=[CH:25][C:26]=3[CH3:27])[C:7]([CH3:8])=[CH:6][N:5]=2)=[CH:11][CH:12]=1)#[N:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2789444-Amino-3,5-dimethylbenzonitrileHCID 86583607HCID 86583607, Verbindung

Produkt 1

HCID 486392HCID 486392, VerbindungAusbeute 202,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344
Dichloromethane
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

4-[[4-[(4-chloro-5-methyl-2-pyrimidinyl]amino]benzonitrile (0.01541 mol), 4-amino-3,5-dimethyl-benzonitrile (0.00219 mol), 1-methyl-2-pyrrolidinone (4 ml), 1,4-dioxane (15 ml) and diisopropylethylamine (0.0154 mol) were combined in a flask under a stream of argon and heated at 160-230° C. for 16 hours. CH2Cl2 and 1N NaOH were added, and the mixture was stirred 1 hour and filtered to give a brown solid (*). The CH2Cl2 filtrate was separated and was evaporated and purified by flash column chromatography (eluent: 2% CH3OH/CH2Cl2). The desired fractions were combined, evaporated and the residue was stirred in CH2Cl2. The solid precipitate was filtered off, combined with the brown solid (*) and recrystallized from CH3CN. The precipitate was filtered off and dried, yielding 1.57 g (29%) of 4-[[2-[(4-cyanophenyl)amino]-5-methyl-4-pyrimidinyl]amino]-3,5-dimethylbenzonitrile (compound 89).

Aufarbeitung

  1. filtrationfiltered
  2. customto give a brown solid (*)
  3. customThe CH2Cl2 filtrate was separated
  4. customwas evaporated
  5. custompurified by flash column chromatography (eluent: 2% CH3OH/CH2Cl2)
  6. customevaporated
  7. stirringthe residue was stirred in CH2Cl2
  8. filtrationThe solid precipitate was filtered off
  9. customrecrystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-813d367786df433c8f44798775937947
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06903213B2

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