Triphenylphosphine → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline

HRID 639961

Reaktionsgleichung

Reaktionsgleichung von HRID 639961
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][CH2:21][CH2:22][CH2:23][OH:24].[Cl:25][C:26]1[C:35]2[C:30](=[CH:31][C:32](O)=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][N:27]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[Cl:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([O:24][CH2:23][CH2:22][CH2:21][Cl:20])=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][N:27]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 123133-Chloro-1-propanolHCID 97268Di-tert-butyl azodicarboxylateHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Produkt 1

HCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazolineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenylphosphine (2.6 g, 10.1 mmol) and 3-chloropropanol (0.69 ml, 8.2 mmol) were added to a suspension of 4-chloro-7-hydroxy-6-methoxyquinazoline (1.65 g, 7.8 mmol) in dichloromethane (100 ml) under argon. The flask was placed in a water bath at 20° C. and di-tertbutyl azodicarboxylate (2.30 g, 10.1 mmol) added portion wise over a few minutes. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated and the solution loaded directly onto a silica chromatography column. Elution with ethyl acetate:petroleum ether (3:7), yielded 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (2.0 g, 91% yield):

Aufarbeitung

  1. customThe flask was placed in a water bath at 20° C.
  2. concentrationThe reaction mixture was concentrated
  3. washElution with ethyl acetate:petroleum ether (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-eb7626e449e04f46aadfe370377ff9e0
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691867B2

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