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Ammonium formate → 5-(4-Amino-2-fluorophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 2067748
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HRID 2067748 반응식
C([N:8]1[C:13](=[O:14])[C:12]2[C:15]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:24]=3[F:32])=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:15]2[C:12]3[C:13](=[O:14])[NH:8][CH:9]=[N:10][C:11]=3[N:18]([CH3:19])[C:17](=[O:20])[C:16]=2[CH3:21])=[C:24]([F:32])[CH:25]=1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 598230393-Benzyl-5-(2-fluoro-4-nitrophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

생성물 1

HCID 1360808875-(4-Amino-2-fluorophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione수율 67.3%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 31275
1,4-Dioxane
용매

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온도
60 °C

실험 절차

3-Benzyl-5-(2-fluoro-4-nitrophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (4.1 mg, 9.42 mmol), palladium hydroxide (20% on carbon, 4 g) and ammonium formate (4 g, 63.4 mmol) were stirred in dioxane (200 mL) at 90° C. for 4 hours in a sealed pressure vessel. The suspension was filtered and the solid refluxed in DMF (20 mL) for 1 hour then filtered. This was repeated 3 times. The filtrates were combined and evaporated. The residue was dissolved in DMF (50 mL) and Quadrapure palladium scavenger (20 g) was added and the mixture stirred at 60° C. overnight. The mixture was filtered and evaporated, ether was added and a precipitate formed. This solid was filtered to give 2 g of the title compound (67%). [M+H] calc'd for C15H14FN5O2, 316; found, 316.

후처리

  1. filtrationThe suspension was filtered
  2. temperaturethe solid refluxed in DMF (20 mL) for 1 hour
  3. filtrationthen filtered
  4. customevaporated
  5. dissolutionThe residue was dissolved in DMF (50 mL)
  6. additionQuadrapure palladium scavenger (20 g) was added
  7. filtrationThe mixture was filtered
  8. customevaporated
  9. additionether was added
  10. customa precipitate formed
  11. filtrationThis solid was filtered

출처 및 근거

ORD 기록
ord-b24585c2098a4c4ea688fb01070f9c27
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08293901B2

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