Sodium hydride → 3-Amino-7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione

HRID 729411

Reaktionsgleichung

Reaktionsgleichung von HRID 729411
[Cl:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[C:10](=[O:11])[NH:9][C:8](=[O:12])[N:7]([CH:13]3[CH2:15][CH2:14]3)[C:6]=2[N:16]=1.[H-].[Na+].[N+:20](C1C=C([N+]([O-])=O)C=CC=1NO)([O-])=O>CN(C)C=O.O1CCOCC1>[NH2:20][N:9]1[C:10](=[O:11])[C:5]2[CH:4]=[C:3]([F:17])[C:2]([Cl:1])=[N:16][C:6]=2[N:7]([CH:13]2[CH2:15][CH2:14]2)[C:8]1=[O:12]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 5743493N-Hydroxy-2,4-dinitrobenzenamineHCID 219795017-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione

Produkt 1

HCID 219791163-Amino-7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dioneAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 217120691,4-dioxane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3.83 g (15 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione (Example 23i) in 50 mL of dimethylformamide-dioxane (1:1) is cooled to 0° C. and treated portionwise with 0.8 g (20 mmol) of 60% sodium hydride/mineral oil. The reaction is stirred to room temperature for 30 minutes, re-cooled to 0° C. and 3.2 g (16 mmol) of 2,4-dinitrophenylhydroxylamine is added all at once. After stirring at room temperature overnight, the dioxane is removed in vacuo and the residue is diluted to 300 mL with ice and water and stirred at 5° C. for 1 hour. The precipitate is removed by filtration, washed with water, ether and dried in vacuo to give 2.65 g of the title compound, mp 192-194° C. A second crop, (0.6 g) could be isolated by evaporating the filtrate and triturating the residue with petroleum ether.

Aufarbeitung

  1. temperaturere-cooled to 0° C.
  2. stirringAfter stirring at room temperature overnight
  3. customthe dioxane is removed in vacuo
  4. additionthe residue is diluted to 300 mL with ice and water
  5. stirringstirred at 5° C. for 1 hour
  6. customThe precipitate is removed by filtration
  7. washwashed with water, ether
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6046dc66b2064085bb558d145553d9bf
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

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