Dimethyl Sulfoxide → Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

HRID 1845264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845264
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.[H-].[Na+].CS(C)=O.Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1>O1CCCC1>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Produkt 1

HCID 58188218Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (300 mg, 1.24 mmol) in tetrahydrofuran (20 mL) at 0° C. was added sodium hydride (60% in mineral oil, 55 mg, 1.37 mmol) over a period of 10 minutes. The reaction mixture was concentrated to afford a green solid. A microwave vial was charged with the resulting green solid, dimethyl sulfoxide (8 mL), and 2-chloropyrimidine (118 mg, 0.98 mmol). The mixture was subjected to microwave irradiation at 100° C. for 4 minutes. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by flash chromatography to afford the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a green solid
  3. customirradiation at 100° C. for 4 minutes
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fbd4bb8346d246af815030e84b257bdd
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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