p-Toluenesulfonic acid → N'-{2,5-dimethyl-4-[2-(methyl-phenyl-amino)-pyrimidin-4-yloxy]-phenyl}-N-ethyl-N-methyl-formamidine

HRID 12081

Reaktionsgleichung

Reaktionsgleichung von HRID 12081
[NH2:1][C:2]1[C:22]([CH3:23])=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)=[C:4]([CH3:24])[CH:3]=1.COC(OC)OC.[C:32]1([CH3:42])C=CC(S(O)(=O)=O)=CC=1.[CH3:43][NH:44][CH2:45]C>>[CH3:23][C:22]1[CH:21]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)[C:4]([CH3:24])=[CH:3][C:2]=1[N:1]=[CH:43][N:44]([CH2:32][CH3:42])[CH3:45]

Komponenten

5

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 67026468[4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine

Produkt 1

HCID 16004709N'-{2,5-dimethyl-4-[2-(methyl-phenyl-amino)-pyrimidin-4-yloxy]-phenyl}-N-ethyl-N-methyl-formamidine

Versuchsvorschrift

To a mixture of 252 mg (0.7 mmol) of [4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine and 4 ml of trimethoxymethane, 20 mg of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 2 hrs and concentrated in vacuo. The mixture was solved in 10 ml of dichloromethane and 62 mg (1.05 mmol) methyl ethyl amine was added. After stirring 18 hrs at ambient temperature the mixture was evaporated and yielded 280 mg (89%) with a purity of 87%; log P (pH 2.3)=1.61.

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 2 hrs
  3. concentrationconcentrated in vacuo
  4. customwas evaporated
  5. customyielded 280 mg (89%) with a purity of 87%

Quellen und Nachweise

ORD-Eintrag
ord-5891a95dbe0a4f5487ba99d0197a9015
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727986B2

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