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Water → 2-chloro-N-(2-chloro-6-methoxy-5-nitropyrimidin-4-yl)-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyaniline

HRID 1513086
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1513086
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([O:12][CH3:13])[N:3]=1.[Cl:14][C:15]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH2:25][C:26]2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[F:34])=[CH:18][C:16]=1[NH2:17].C(N(CC)C(C)C)(C)C.O>C(#N)C>[Cl:14][C:15]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH2:25][C:26]2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[F:34])=[CH:18][C:16]=1[NH:17][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([O:12][CH3:13])[N:3]=[C:2]([Cl:1])[N:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 593096572-Chloro-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyanilineHCID 593099452,4-Dichloro-5-nitro-6-methoxypyrimidine

Produkt 1

HCID 867615882-chloro-N-(2-chloro-6-methoxy-5-nitropyrimidin-4-yl)-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyanilineAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 2,4-dichloro-6-methoxy-5-nitropyrimidine (1.79 g) in acetonitrile (21 mL) were added 2-chloro-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyaniline (2.18 g) and N,N-diisopropylethylamine (1.28 mL), and the mixture was stirred at 40° C. for 3 days. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/ethyl acetate=3/1), and collected by filtration. The collected solids were dried under reduced pressure to give 2-chloro-N-(2-chloro-6-methoxy-5-nitropyrimidin-4-yl)-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyaniline (3.15 g). The title compound was prepared in a similar manner to that described in Example 397 using this material instead of 2-chloro-N-(2-chloro-6-methoxy-5-nitropyrimidin-4-yl)-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyaniline.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. filtrationcollected by filtration
  6. customThe collected solids were dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f31d913764d240b5a8a723cf2306b80d
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217069B2

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