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

HRID 729411

반응식

HRID 729411 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 217120691,4-dioxane N,N-dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6046dc66b2064085bb558d145553d9bf
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

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