p-Toluenesulfonic acid monohydrate → Methyl 4-(4-fluoro-2-isopropoxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

HRID 532306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532306
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([O:24][CH:25]([CH3:27])[CH3:26])[CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:12]2[C:7]3[C:6]([CH3:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[S:14][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:19]([O:24][CH:25]([CH3:27])[CH3:26])[CH:18]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 37563854-Fluoro-2-(1-methylethoxy)benzenamine

Produkt 1

HCID 46182043Methyl 4-(4-fluoro-2-isopropoxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (112 mg), 4-fluoro-2-isopropoxyaniline (77.9 mg) and p-toluenesulfonic acid monohydrate (15 mg) were dissolved in dioxane (3.0 ml). The reaction was heated at 110° C. under microwave irradiation. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane and extracted with water. The organic phase was dried and concentrated in vacuo. The residue was triturated with diisopropyl ether and filtered.

Aufarbeitung

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionextracted with water
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7a607f1f638641e6a9b8c8d92198a95a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853193B2

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