Pyridine → HCID 18925013, Verbindung

HRID 1288873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1288873
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[C:28]([C:30]1[CH:31]=[C:32]([C:34]([CH3:37])=[CH:35][CH:36]=1)[NH2:33])#[CH:29]>CN(C=O)C>[ClH:1].[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[N:5]=[CH:4][N:3]=[C:2]2[NH:33][C:32]1[CH:31]=[C:30]([C:28]#[CH:29])[CH:36]=[CH:35][C:34]=1[CH3:37]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineHCID 189250605-Ethynyl-2-methylaniline

Produkt 1

HCID 18925013HCID 18925013, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chloro-6,7-bis-(2-methoxy-ethoxy)-quinazoline (153 mg, 0.49 mmol), pyridine (40 μL) and 3-ethynyl-6-methylaniline (71 mg, 0.54 mmol) were reacted in DMF (3 mL) at 110° C. under an atmosphere of N2 for 36 hours. The solvent was removed in vacuo and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was chromatographed on silica using 40% acetone/CH2Cl2 to provide 40 mg (19%) of pure product as its free base. This oil was dissolved in a minimum volume of CHCl3, diluted with several volumes of ether, and triturated with 1M HCl in ether to precipitate the title product as a white solid (M.P. 170°-185° C. (dec); LC-MS: 408 (MH+); anal. RP18-HPLC RT: 3.93 min.).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on silica using 40% acetone/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-900dfdd3833444929473187836ca8f1c
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747498

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