1-Bromooctane → 2-(2,3-Difluoro-4-octyloxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

HRID 376769ノート

反応式

HRID 376769 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:21]=2)=[CH:12][N:11]=1.[H-].[Na+].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:21]=2)=[CH:12][N:11]=1

参加物

5

反応物 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 1355974452-(2,3-Difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

生成物 1

HCID 193591142-(2,3-Difluoro-4-octyloxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 2.4 mmol of 2-(2,3-difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine in 10 ml of DMF is added dropwise at room temperature and under a protective gas to a suspension of 2.7 mmol of sodium hydride (80 percent in mineral oil) in 5 ml of dry DMF. The mixture is stirred for a further 30 minutes, and 2.7 mmol of 1-bromooctane, dissolved in 10 ml of DMF, are then added slowly. The reaction mixture is stirred at room temperature for 20 hours and introduced into 100 ml of ice/water, the mixture is extracted a number of times with dichloromethane, and the combined organic extracts are washed with sat. sodium chloride solution and dried using magnesium sulfate. After the solvent has been removed in vacuo, the crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent and recrystallized from acetonitrile, giving 0.77 g (61%) of colorless crystals, X 89 S3 73.5 SC 164 SA 167 I.

後処理

  1. additionare then added slowly
  2. stirringThe reaction mixture is stirred at room temperature for 20 hours
  3. extractionthe mixture is extracted a number of times with dichloromethane
  4. washthe combined organic extracts are washed with sat. sodium chloride solution
  5. customdried
  6. customAfter the solvent has been removed in vacuo
  7. customthe crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent
  8. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-d734b56d47bc4303be866366e25ed15b
出典データセット
uspto-grants-2000_02
特許番号
US06022492

反応ノート

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