Water → HCID 53330914、化合物

HRID 1260311ノート

反応式

HRID 1260311 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)=[CH:4][CH:3]=1.C[Al](C)C.C([O:20][C:21]([C:23]1[C:28]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[N:34][CH:35]=2)=[CH:27][CH:26]=[C:25]([CH3:36])[N:24]=1)=O)C.O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:21]([C:23]3[C:28]([NH:29][C:30]4[CH:35]=[N:34][CH:33]=[N:32][CH:31]=4)=[CH:27][CH:26]=[C:25]([CH3:36])[N:24]=3)=[O:20])=[N:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 136269441-(4-FLUORO-PHENYL)-1H-PYRAZOL-3-AMINEHCID 16682925TrimethylaluminumHCID 58368053Ethyl 6-methyl-3-(5-pyrimidinylamino)-2-pyridinecarboxylate

生成物 1

HCID 53330914HCID 53330914、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

1-(4-Fluoro-phenyl)-1H-pyrazol-3-ylamine (55 mg, 0.31 mmol) was dissolved under inert gas atmosphere in dioxane (2 ml) and trimethylaluminium (0.154 ml, 2M toluene solution) was added. After stirring for 30 min at ambient temperature, 6-methyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (A-1; 20 mg, 0.08 mmol) was added and the reaction mixture was heated at reflux for 18 hours. Upon cooling to room temperature water (0.5 ml) was added and intensive stirring was continued for 5 min. Sufficient sodium sulfate for water absorption and dichloromethane were added while stirring is continued. The resulting solution was then filtered through decalite and washed with dichloromethane. The solvent was evaporated and the final product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as off-white solid (5 mg, 16%).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. additionwas added
  4. stirringintensive stirring
  5. waitwas continued for 5 min
  6. customSufficient sodium sulfate for water absorption and dichloromethane
  7. additionwere added
  8. stirringwhile stirring
  9. filtrationThe resulting solution was then filtered through decalite
  10. washwashed with dichloromethane
  11. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-2adae1deadec4637bc1e209228e41307
出典データセット
uspto-grants-2013_06
特許番号
US08470820B2

反応ノート

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