Sodium Hydroxide → 5-Cyano-4-phenyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine

HRID 1370066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370066
[N+]([O-])([O-])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:17][C:18]([NH2:20])=[NH2+:19])[CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14].[C:21]1([C:27](=O)[C:28]([C:33]#N)=[CH:29][N:30](C)C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C(O)C>[C:29]([C:28]1[C:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:19][C:18]([NH:17][C:9]2[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=2)=[N:20][CH:33]=1)#[N:30]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileHCID 178419082HCID 178419082, Verbindung

Produkt 1

HCID 98203645-Cyano-4-phenyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amineAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3,4,5-trimethoxyphenylguanidinium nitrate (1.44 g, 5.0 mmol), 1-phenyl-2-cyano-3-dimethylaminopropen-1-one (1.0 g, 5.0 mmol) and sodium hydroxide (0.22 g, 5.5 mmol) in ethanol (20 ml) was heated at reflux for 18 h. On cooling the resulting precipitate was collected by filtration, washed with water and diethyl ether, then dried to give the title compound (895 mg) as a green solid m.p. 246°. δH (d6DMSO) 10.37 (1H, br s), 8.93 (1H, s), 7.99 (2H, m), 7.60 (3H, m), 7.25 (2H, m), 3.75 (6H, s) and 3.63 (3H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureOn cooling the resulting precipitate
  4. filtrationwas collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ae90bc59464b4eb090e95ada81b2db1f
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579983B1

Notizen zur Reaktion

Wird geladen…