p-Toluenesulfonic acid → Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

HRID 240598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240598
[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].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH4+].[OH-]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[OH:24])[C:7]=2[C:6]=1[CH3:15])=[O:4]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 14923Ammonium HydroxideHCID 1857632-Amino-5-fluorophenolHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Produkt 1

HCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (2.43 g), 2-amino-5-fluorophenol (2.43 g) and p-toluenesulfonic acid (190.0 mg) were dissolved in dioxane (50.0 ml) and heated at 120° C. for 4 h under nitrogen. The reaction mixture was allowed to cool and treated with 3M NH4OH. The resultant suspension was filtered, the solid was washed with ether and dried in vacuo at 60° C. over P2O5.

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe resultant suspension was filtered
  3. washthe solid was washed with ether
  4. dry with materialdried in vacuo at 60° C. over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-cf324c23c5ed405093e176a4ce654e97
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648068B2

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