Reaktion #10422

Reaktionsgleichung

2,4-dinitrophenylhydroxylamine

1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid

sodium hydride

→

title compound

Ausbeute 76.7%

3-Amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid

Ausbeute 76.7%

Lösungsmittel

dimethylformamide dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at room temperature overnight
2. 2
   Sonstigethe dioxane is removed in vacuo
3. 3
   workup.ADDITIONthe residue is diluted to 100 mL with ice and water
4. 4
   workup.STIRRINGstirred at 5° C. for 1 hour
5. 5
   ExtraktionThe aqueous solution is extracted with ethyl acetate (3×50 mL) with the combined organic layers
6. 6
   Waschenbeing washed with water
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated in vacuo

Vorschrift

A solution of 0.47 g (1.57 mmol) of 1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid (Example 35) in 20 mL of dimethylformamide/dioxane (1:1) is treated portionwise with 0.08 g (2.0 mmol) of 60% sodium hydride/mineral oil. The reaction is stirred at room temperature for 1 hour and 0.32 g (1.6 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 100 mL with ice and water and stirred at 5° C. for 1 hour. The aqueous solution is extracted with ethyl acetate (3×50 mL) with the combined organic layers being washed with water, dried (MgSO4), filtered and evaporated in vacuo to give 0.4 g of the title compound, mp 167–169° C.

Quelle