Sodium hydride → 2-[N-Cyclopropylmethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acid

HRID 1097387ノート

反応式

HRID 1097387 の反応式
[H-].[Na+].[CH:3]1[C:14]2=[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]3=[CH:5][C:4]=1[NH:16][C:17]1[N:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:18]=1.Br[CH2:29][CH:30]1[CH2:32][CH2:31]1.[Cl-].[NH4+]>CN(C)C=O>[CH:32]1([CH2:31][N:16]([C:4]2[CH:3]=[C:14]3[C:15]4[CH:10]([CH2:11][CH2:12][CH2:13]3)[CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=2)[C:17]2[N:18]=[CH:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:30][CH2:29]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 66811056Ethyl 2-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylate

生成物 1

HCID 585265572-[N-Cyclopropylmethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acid収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of sodium hydride (60%, 0.009 g) in N,N-dimethylformamide (2 ml) was added with ethyl 2-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylate (0.035 g) dissolved in N,N-dimethylformamide (1 ml), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with bromomethylcyclopropane (0.025 ml), and the mixture was stirred overnight. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, the resulting residue was suspended in ethanol (5 ml), the suspension was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5) to obtain the title compound (0.039 g, yield: 96%) as pale yellow amorphous.

後処理

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additionthe suspension was added with 20% aqueous sodium hydroxide (1 ml)
  7. stirringthe mixture was stirred at 50° C. for 3 hours
  8. waitThe reaction mixture was left
  9. temperatureto cool
  10. extractionthe mixture was extracted with chloroform
  11. washThe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationThe organic layer was concentrated under reduced pressure
  14. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5)

出典と根拠

ORDレコード
ord-9b34d58fb5914a138d75e73c0a80ddc4
出典データセット
uspto-grants-2012_03
特許番号
US08143260B2

反応ノート

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