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Ammonium Chloride → 2-{5-{[4-Butyl-1-(5-methoxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile

HRID 1622976
ノート
印刷プレビュー

反応式

HRID 1622976 の反応式
C[Al](C)C.[NH2:5][C:6]1[N:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][N:7]=1.[C:14]([NH:17]/[C:18](/[CH2:39][CH2:40][CH2:41][CH3:42])=[C:19](/[CH2:24][C:25]1[CH:26]=[N:27][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]#[N:38])=[CH:29][CH:30]=1)\[C:20](OC)=[O:21])(=O)[CH3:15].[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl.ClCCCl>[CH2:39]([C:18]1[N:17]=[C:14]([CH3:15])[N:5]([C:6]2[N:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][N:7]=2)[C:20](=[O:21])[C:19]=1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]#[N:38])=[N:27][CH:26]=1)[CH2:40][CH2:41][CH3:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 23052442-Amino-5-methoxypyrimidineHCID 16682925TrimethylaluminumHCID 86667259methyl (Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoate

生成物 1

HCID 679794502-{5-{[4-Butyl-1-(5-methoxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile収率 77%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒2 回HCID 6212Chloroform溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

Process 3: Under argon atmosphere, trimethylaluminum (2 mol/L hexane solution, 1.45 mL, 2.90 mmol) was added to 1,2-dichloroethane (30 mL) solution of 2-amino-5-methoxypyrimidine (220 mg, 1.74 mmol) at room temperature, and stirred at the same temperature for 80 minutes. 1,2-dichloroethane (20 mL) solution of methyl(Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoate (227 mg, 0.58 mmol) was added dropwise thereto at room temperature followed by reflux for 17 hours under heating. An aqueous solution of ammonium chloride and chloroform were added to the reaction mixture, which was then filtered through a pad of celite. The organic layer in the filtrate was separated, and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residues obtained were subjected to silica gel column chromatography (hexane/ethyl acetate=2:1) to obtain 2-{5-{[4-butyl-1-(5-methoxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile (207 mg, 77%) as a yellow oil.

後処理

  1. customat room temperature
  2. temperatureby reflux for 17 hours
  3. temperatureunder heating
  4. filtrationwas then filtered through a pad of celite
  5. customThe organic layer in the filtrate was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residues obtained

出典と根拠

ORDレコード
ord-318796b2df0b47129e7ecb2c0dd28a47
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778954B2

反応ノート

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