Potassium Carbonate → 4-(2-Cyclobutoxy-4-fluoro-phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 406104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406104
[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[OH:21])[C:7]=2[C:6]=1[CH3:23])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:31]1[CH2:34][CH2:33][CH2:32]1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:7]=2[C:6]=1[CH3:23])=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Produkt 1

HCID 584218024-(2-Cyclobutoxy-4-fluoro-phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4-(4-fluoro-2-hydroxy-phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (200 mg), potassium carbonate (166 mg) and bromocyclobutane (113 μl) in DMF (3 ml) was stirred at 60° C. over the weekend. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was concentrated and the residue was triturated with diethyl ether to give the desired compound.

Aufarbeitung

  1. washwashed with water and brine
  2. concentrationThe organic layer was concentrated
  3. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1088eb0a6b9e4ff8af0405e32c9375a3
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754079B2

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