Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (5-[(2,6-Difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-ethyl-amine

HRID 459950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459950
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[NH2:13].[CH2:14]([NH:16][C:17]1[C:22]([CH:23]=O)=[CH:21][N:20]=[C:19]([S:25][CH3:26])[N:18]=1)[CH3:15].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]=[CH:23][C:22]1[C:17]([NH:16][CH2:14][CH3:15])=[N:18][C:19]([S:25][CH3:26])=[N:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Produkt 1

HCID 18444815(5-[(2,6-Difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-ethyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

In a 500-mL round bottom flask, 3.00 g (15.86 mmol) of 2,6-difluoro-3,5-dimethoxy-phenylamine and 3.13 g (15.86 mmol) of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde in 150 mL of toluene with 1.11 g (4.76 mmol) of camphorsulfonic acid was fitted with a Dean Stark trap and heated at reflux. During the day, the toluene was drained 3 times from the finger, replenished with 100 mL of the solvent and continued heating at reflux under nitrogen atmosphere overnight. The toluene was concentrated in vacuo and dried to give 7.19 g (quantitative) of the title compound. No further purification was necessary. MS (APCI) (m+1)/z 369.1.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux
  3. temperaturecontinued heating
  4. temperatureat reflux under nitrogen atmosphere overnight
  5. concentrationThe toluene was concentrated in vacuo
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-02b9c45d8b1840fd81c7ef9f9f0a5932
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196090B2

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