Ethyl Acetate → 4-[4-Fluoro-2-(1-methanesulfonyl-pyrrolidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 240603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240603
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([OH:23])[CH:3]=1.CS(O[CH:29]1[CH2:33][CH2:32][N:31]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:30]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH3:22][O:21][C:19]([C:16]1[S:15][C:11]2[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[O:23][CH:29]3[CH2:33][CH2:32][N:31]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:30]3)[C:10]=2[C:17]=1[CH3:18])=[O:20]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 190775631-(Methylsulfonyl)pyrrolidin-3-yl methanesulfonateHCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Produkt 1

HCID 584130244-[4-Fluoro-2-(1-methanesulfonyl-pyrrolidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (described in V.1) (1.0 g), 1-(methylsulfonyl)pyrrolidin-3-yl methansulfonate and potassium carbonate (664.0 mg) were combined in DMF (15.0 ml) and heated at 60° C. overnight. The temperature was increased at 80° C. and heated for 6 h again. The reaction mixture was allowed to cool overnight. The mixture was portioned between EtOAc and water. The suspension was fitlered, solid washed with EtOAc and air-dried under vacuum.

Aufarbeitung

  1. temperatureThe temperature was increased at 80° C.
  2. temperatureheated for 6 h again
  3. temperatureto cool overnight
  4. washsolid washed with EtOAc
  5. customair-dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-137750befbf14ee493392e27b5bab155
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648068B2

Notizen zur Reaktion

Wird geladen…