Hydrochloric Acid → 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-morpholinophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 401034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401034
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[C:32]=1[OH:33])[CH:28]=O)[CH3:23].[NH2:37][C:38]([NH2:40])=[O:39].Cl>CCO>[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH:28]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:8][CH:9]=3)[NH:40][C:38](=[O:39])[NH:37]2)[CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[C:32]=1[OH:33])[CH3:23]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2696961-[4-(Morpholin-4-yl)phenyl]-2-phenylethanone2×HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Produkt 1

HCID 569616134-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-morpholinophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-oneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-morpholinophenyl)-2-phenylethanone (Intermediate 25) (280 mg, 1.00 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (175 mg, 0.83 mmol), urea (179 mg, 2.99 mmol), and concentrated HCl solution (0.07 mL, 0.83 mmol) in EtOH (5 mL) was refluxed for 48 h. The mixture was evaporated in vacuo, and the residue was purified by preparative HPLC to give Compound 56 (55.29 mg, yield 13%) as a solid. 1H NMR (CD3OD 300 MHz): δ 7.62 (d, J=2.1 Hz, 1H), 7.20-7.15 (m, 3H), 7.10-7.04 (m, 3H), 6.92-6.85 (m, 4H), 5.30 (s, 1H), 4.12-4.02 (m, 2H), 3.81 (t, J=4.8 Hz, 4H), 3.15 (t, J=4.8 Hz, 4H), 1.41 (t, J=6.9 Hz, 3H); MS (ESI): m/z 517.0 [M+1]+.

Aufarbeitung

  1. temperaturewas refluxed for 48 h
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7e06dab3789b41b4baa90af36026fa71
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741915B2

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