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

HRID 10325ノート

反応式

HRID 10325 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 219791163-Amino-7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione収率 65.3%

試薬・触媒・溶媒 1

HCID 217120691,4-dioxane N,N-dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-185d4e0e534448e7ba4c8a2b3a5896e9
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

反応ノート

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