Реакция #10421

Уравнение реакции

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

sodium hydride

2,4-dinitrophenylhydroxylamine

→

title compound

Выход 65.3%

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

Выход 65.3%

Растворители

dimethylformamide dioxane

Условия реакции

Обработка

1. 1
   Температураre-cooled to 0° C.
2. 2
   workup.STIRRINGAfter stirring at room temperature overnight
3. 3
   Другоеthe dioxane is removed in vacuo
4. 4
   workup.ADDITIONthe residue is diluted to 300 mL with ice and water
5. 5
   workup.STIRRINGstirred at 5° C. for 1 hour
6. 6
   ДругоеThe precipitate is removed by filtration
7. 7
   Промывкаwashed with water, ether
8. 8
   Другоеdried in vacuo

Методика

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.

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