Trimethyl orthoformate → 5-((5-Fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 40360

Reaktionsgleichung

Reaktionsgleichung von HRID 40360
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH:11](OC)(OC)OC.[F:18][C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[N:23][CH:24]=1>CCCCCC>[F:18][C:19]1[CH:20]=[C:21]([NH:25][CH:11]=[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:9])[CH:22]=[N:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 5744505-Fluoro-3-pyridinamine

Produkt 1

HCID 675034075-((5-Fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 150 mL sealed tube was charged with 2,2-dimethyl-1,3-dioxane-4,6-dione (6.0 g, 41.6 mmol) and trimethyl orthoformate (41.6 mL, 41.6 mmol). This was heated to 100° C., and stirred at this temperature for 2 hours. Reaction then cooled to 30° C. and 5-fluoropyridin-3-amine (4.7 g, 41.6 mmol) added portion-wise. Reaction vessel resealed and mixture stirred at 100° C. for 3 hours. LC/MS shows completion. Reaction mixture was cooled to room temperature, diluted with hexane, filtered, and air dried to yield 5-((5-fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (9.1 g, 82% yield) as a bright yellow solid. MS [M+H]=267.2. Calc'd for C12H11FN2O4=266.2.

Aufarbeitung

  1. customA 150 mL sealed tube
  2. customReaction
  3. temperaturethen cooled to 30° C.
  4. customReaction vessel
  5. stirringmixture stirred at 100° C. for 3 hours
  6. customReaction mixture
  7. temperaturewas cooled to room temperature
  8. filtrationfiltered
  9. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-a27c34caba144fe9ae34d3fccb51d828
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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