Methyl formate → methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoate

HRID 474714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474714
[H-].[Na+].[CH:3]([O:5][CH3:6])=[O:4].[F:7][C:8]([F:22])([F:21])[C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](OC)=[O:18])=[CH:11][N:10]=1>COCCOC>[OH:18]/[CH:17]=[C:16](/[CH2:15][C:12]1[CH:11]=[N:10][C:9]([C:8]([F:22])([F:21])[F:7])=[N:14][CH:13]=1)\[C:3]([O:5][CH3:6])=[O:4]

Komponenten

5

Edukt 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 21936211Methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate

Produkt 1

HCID 67953508methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a solution of NaH (360 mg, 9.00 mmol) in DME (20 mL) was added a solution of methyl formate (0.254 mL, 4.10 mmol) and methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate (800 mg, 3.42 mmol) in DME (20 mL) at 0° C. The mixture was stirred at room temperature overnight, and quenched with MeOH. Purification via reverse phase flash chromatography afforded the title compound (730 mg, 2.78 mmol, 82% yield) as yellow solid. LCMS: rt=2.03 min, [M+H+]=263.

Aufarbeitung

  1. customquenched with MeOH
  2. customPurification via reverse phase flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f1ff2c5bd4a04857acab803daf319a93
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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