Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → (+/-)-5,8-Dihydro-4-methoxy-7-methyl-5-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid isopropyl ester

HRID 34527

Reaktionsgleichung

Reaktionsgleichung von HRID 34527
[CH:1]([O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:9]2[C:14](=[O:15])[NH:13][CH:12]=[N:11][C:10]=2[NH:16][C:17]=1[CH3:18])=[O:6])([CH3:3])[CH3:2].[CH3:28][O+](C)C.F[B-](F)(F)F>ClCCCl>[CH:1]([O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:9]2[C:14]([O:15][CH3:28])=[N:13][CH:12]=[N:11][C:10]=2[NH:16][C:17]=1[CH3:18])=[O:6])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 136393698(+/-)-3,4,5,8-Tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]-pyrimidine-6-carboxylic acid isopropyl ester

Produkt 1

HCID 13645046(+/-)-5,8-Dihydro-4-methoxy-7-methyl-5-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid isopropyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Three and 0.7 g (10 mmol) (±)-3,4,5,8-tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]-pyrimidine-6-carboxylic acid isopropyl ester and 3.0 g (20 mmol) trimethyloxonium-tetrafluoroborate are stirred in 150 ml 1,2-dichloroethane in nitrogen atmosphere and at room temperature for three hours. The product is extracted twice with 50 ml saturated sodium hydrogen carbonate solution, the organic phase is separated, dried over sodium sulfate and reduced under vacuum. Twice recrystallizing the residue from diisopropyl ether/isopropanol yields the product in the form of colorless crystals with a mp of 212°-213° C.

Aufarbeitung

  1. extractionThe product is extracted twice with 50 ml saturated sodium hydrogen carbonate solution
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customTwice recrystallizing the residue from diisopropyl ether/isopropanol
  5. customyields the product in the form of colorless crystals with a mp of 212°-213° C.

Quellen und Nachweise

ORD-Eintrag
ord-e09c11473fef44f999758252a4e6c990
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762837

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