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Tetrahydrofuran → 1-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 915948
ノート
印刷プレビュー

反応式

HRID 915948 の反応式
C([Li])CCC.O1CCCC1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:19][C:20](=[O:34])[C:21]3[N:26]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[N:25]=[C:24]([CH3:33])[C:22]=3[N:23]=2)=[C:14]([O:35][CH3:36])[CH:13]=1.[CH3:37][N:38]1[CH2:43][CH2:42][C:41](=[O:44])[CH2:40][CH2:39]1>O>[CH:27]1([N:26]2[C:21]3[C:20](=[O:34])[NH:19][C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:41]5([OH:44])[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]5)=[CH:13][C:14]=4[O:35][CH3:36])=[N:23][C:22]=3[C:24]([CH3:33])=[N:25]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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

6

反応物 4

HCID 8028TetrahydrofuranHCID 740491-Methyl-4-piperidoneHCID 136005882HCID 136005882、化合物HCID 178418339Butyllithium

生成物 1

HCID 1360059331-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one収率 55.1%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
-78 °C

実験手順

In an atmosphere of argon, 0.95 ml of n-butyl lithium (1.59M/hexane solution, 1.51 mmol) was added dropwise at −78° C. to a 10 ml anhydrous tetrahydrofuran solution of 300 mg (0.72 mmol) of the compound obtained in Example 15. The mixture was stirred at −78° C. for 30 minutes, and then 133 μl (1.08 mmol) of 1-methyl-4-piperidone was added, followed by heating the mixture gradually to 0° C. over the course of 1 hour. Then, water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain 179 mg (55%) of the captioned compound.

後処理

  1. temperatureby heating the mixture gradually to 0° C. over the course of 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

出典と根拠

ORDレコード
ord-0dccdb9d2a3b42118bb24c3baa76b994
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07268128B2

反応ノート

読み込み中…

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