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Triphenylphosphine → 7-((2-Chloro-6-methyl-4-pyridyl)methoxy)-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline

HRID 1737535
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1737535
N(C(OCC)=O)=NC(OCC)=O.Cl.[F:14][C:15]1[CH:34]=[C:33]([CH3:35])[C:32]([O:36][C:37]([O:39][CH3:40])=[O:38])=[CH:31][C:16]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([OH:30])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:60][C:61]1[CH:66]=[C:65]([CH2:67]O)[CH:64]=[C:63]([CH3:69])[N:62]=1>C(Cl)Cl>[Cl:60][C:61]1[CH:66]=[C:65]([CH2:67][O:30][C:24]2[CH:23]=[C:22]3[C:27]([C:18]([NH:17][C:16]4[CH:31]=[C:32]([O:36][C:37]([O:39][CH3:40])=[O:38])[C:33]([CH3:35])=[CH:34][C:15]=4[F:14])=[N:19][CH:20]=[N:21]3)=[CH:26][C:25]=2[O:28][CH3:29])[CH:64]=[C:63]([CH3:69])[N:62]=1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanolHCID 1356711794-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

Produkt 1

HCID 226249947-((2-Chloro-6-methyl-4-pyridyl)methoxy)-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline
Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (296 μl, 1.88 mmol) was added dropwise to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (350 mg, 0.94 mmol), (prepared as described for the starting material in Example 22), triphenylphosphine (492 mg, 1.88 mmol) and 2-chloro-4-hydroxymethyl-6-methylpyridine (178 mg, 1.12 mmol) in methylene chloride (30 ml) and the mixture stirred for 30 minutes at ambient temperature. The solvent was removed by evaporation and the residue was purified by column chromatography eluting with ethyl acetate/methylene chloride (75/25). The purified product was triturated with ether, the solid collected by filtration, washed with ether and dried under vacuum to give 7-((2-chloro-6-methyl-4-pyridyl)methoxy)-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline (373 mg, 78%).

Aufarbeitung

  1. custom(prepared
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by column chromatography
  4. washeluting with ethyl acetate/methylene chloride (75/25)
  5. customThe purified product was triturated with ether
  6. filtrationthe solid collected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f22e6816742043f6adccf22ae3ca33b2
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05962458

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