Sodium Methoxide → 6-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one

HRID 1091398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091398
Cl[C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][C@@H:17]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[CH2:16]3)[N:12]([CH3:28])[C:11](=[O:29])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][O-:31].[Na+]>O1CCCC1>[Cl:8][C:7]1[C:2]([O:31][CH3:30])=[N:3][CH:4]=[CH:5][C:6]=1[C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][C@@H:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:16]2)[N:12]([CH3:28])[C:11](=[O:29])[CH:10]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 57877719HCID 57877719, Verbindung

Produkt 1

HCID 578776496-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-oneAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 6-(2,3-dichloropyridin-4-yl)-2-((2S)-2-(4-fluorophenyl)morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.50 g, 1.15 mmol), and sodium methoxide (1.1 g, 20.4 mmol) in tetrahydrofuran (10 ml) was heated at 60° C. for 5 hours. The resulting suspension was partitioned between chloroform and brine and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 6-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.27 g, 0.58 mmol, 50%) as white crystals.

Aufarbeitung

  1. customThe resulting suspension was partitioned between chloroform and brine
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting 5-10% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-42f526c4d7b448fa99ee16304e3c9fc9
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129377B2

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