Potassium Carbonate → 6-(6-Benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

HRID 556383

Reaktionsgleichung

Reaktionsgleichung von HRID 556383
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[C:15]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=2[O:13][CH:12]=1)=[O:10].[CH2:21]([O:28][CH2:29][C:30]1[CH:35]=[C:34](Cl)[N:33]=[CH:32][N:31]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN1C(=O)CCC1.O.CCOC(C)=O>[CH3:7][O:8][C:9]([C:11]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:34]3[CH:35]=[C:30]([CH2:29][O:28][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:31]=[CH:32][N:33]=3)=[CH:19][C:14]=2[O:13][CH:12]=1)=[O:10]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 534212594-((Benzyloxy)methyl)-6-chloropyrimidineHCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

Produkt 1

HCID 575564436-(6-Benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

415 mg (3.0 mMol) K2CO3 and 249 mg (1.5 mMol) KI are added to a solution of 192 mg (1.00 mMol) 6-hydroxy-benzofuran-3-carboxylic acid methyl ester (Step 9.4) and 258 mg (1.1 mMol) 4-benzyloxymethyl-6-chloro-pyrimidine (commercially available; [CAS: 914802-11-2]) in 1.6 ml NMP. This mixture is stirred for 4 h at 100° C., cooled to rt and diluted with water and EtOAc. The aq. phase is separated off and extracted twice with EtOAc. The organic layers are washed with a diluted solution of Na2S2O3 and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 19:1→1:1) and crystallization from hexane gives the title compound: m.p.: 85-86° C.; MS: [M+1]+=391; TLC(hexane/EtOAc 2:1): Rf=0.38.

Aufarbeitung

  1. temperaturecooled to rt
  2. customThe aq. phase is separated off
  3. extractionextracted twice with EtOAc
  4. washThe organic layers are washed with a diluted solution of Na2S2O3 and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customChromatography (Combi Flash; hexane/EtOAc 19:1→1:1) and crystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-6b4150011eca45b9b4b8893a1e8d51b9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

Verknüpfte Notizen

Wird geladen…