Sodium Hydroxide → N-(4-(2,4-Dimethyl-thiazol-5-YL)-pyrimidin-2-YL)-N',N'-dimethyl-benzene-1,4-diamine

HRID 47212

Reaktionsgleichung

Reaktionsgleichung von HRID 47212
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[S:4][C:3]=1/[CH:8]=[CH:9]/[C:10](N(C)C)=O.[CH3:15][N:16]([CH3:27])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH2:26])=[NH:25])=[CH:19][CH:18]=1.[OH-].[Na+]>O(CCO)C>[CH3:15][N:16]([CH3:27])[C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24]2[N:26]=[C:8]([C:3]3[S:4][C:5]([CH3:7])=[N:6][C:2]=3[CH3:1])[CH:9]=[CH:10][N:25]=2)=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178482866HCID 178482866, Verbindung

Produkt 1

HCID 447962N-(4-(2,4-Dimethyl-thiazol-5-YL)-pyrimidin-2-YL)-N',N'-dimethyl-benzene-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (0.95 mmol, 0.19 g) and N-(4-dimethylamino-phenyl)-guanidine (2 mmol) in 2-methoxylethanol (5 mL) was added NaOH (40 mg). The reaction mixture was heated at 120° C. for 18 h. The solvent was evaporated and the residue was purified by chromatography, using EtOAc/PE to afford N,N-dimethyl-N′-{4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl}-benzene-1,4-diamine {119} (74 mg) as a reddish-brown solid. 1H-NMR (300 MHz, d6-DMSO) δ2.62 (s, 3H, CH3), 2.65 (s, 3H, CH3), 2.86 (s, 6H, CH3), 6.73 (m, 2H, Ph-H), 6.97 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 7.56 (m, 2H, Ph-H), 8.44 (d, 1H, J=5.0 Hz, pyrimidinyl-H), 9.33 (s, 1H, NH). DE MALDI-TOF MS: {M+H}+=329.51 (C17H19N5S requires 325.43).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b03dca88b44849e591e1aa4e724ccab8
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699854B2

Verknüpfte Notizen

Wird geladen…