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Water → 2-(Ethylsulfanyl)-4-oxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,4-dihydropyrido[2,3-d]pyrimidine-7-carbaldehyde

HRID 570724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 570724
[CH2:1]([S:3][C:4]1[N:5]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][CH:18]=2)[C:6](=[O:16])[C:7]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[N:10][C:8]=2[N:9]=1)[CH3:2].C(N(CC)CC)C.O>CS(C)=O>[CH2:1]([S:3][C:4]1[N:5]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[CH:19][CH:18]=2)[C:6](=[O:16])[C:7]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[N:10][C:8]=2[N:9]=1)[CH3:2]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 866853842-(ethylsulfanyl)-7-(hydroxymethyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Produkt 1

HCID 866853852-(Ethylsulfanyl)-4-oxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,4-dihydropyrido[2,3-d]pyrimidine-7-carbaldehydeAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

2-(Ethylsulfanyl)-7-(hydroxymethyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (373 mg) and triethylamine (6 ml) were dissolved in dimethyl sulfoxide (18 ml), sulfur trioxide pyridine complex (1.16 g) was added thereto by several portions, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, 1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (299 mg) as a orange solid.

Aufarbeitung

  1. additionsulfur trioxide pyridine complex (1.16 g) was added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water, 1M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-39d21e097cfc48adba37fbc1788bb495
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09023858B2

Notizen zur Reaktion

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