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

HRID 1660891
ノート
印刷プレビュー

反応式

HRID 1660891 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-67a41a38e89a47e2aea549663580a528
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030317B2

反応ノート

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