Sodium hydride → N-{6-[2-(5-Bromo-pyrimidin-2-yloxy)-ethoxy]-2-propyl-5-p-tolyl-pyrimidin-4-yl}-4-tert-butyl-benzenesulfonamide

HRID 2291

反応式

HRID 2291 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[C:21]([O:30][CH2:31][CH2:32][OH:33])[N:20]=[C:19]([CH2:34][CH2:35][CH3:36])[N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:38]1[N:43]=[CH:42][C:41]([Br:44])=[CH:40][N:39]=1>O1CCCC1.CC(N(C)C)=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]2[C:22]([C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[C:21]([O:30][CH2:31][CH2:32][O:33][C:38]3[N:43]=[CH:42][C:41]([Br:44])=[CH:40][N:39]=3)[N:20]=[C:19]([CH2:34][CH2:35][CH3:36])[N:18]=2)(=[O:14])=[O:15])=[CH:11][CH:12]=1)([CH3:5])([CH3:6])[CH3:4]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 196894984-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide

生成物 1

HCID 19689505N-{6-[2-(5-Bromo-pyrimidin-2-yloxy)-ethoxy]-2-propyl-5-p-tolyl-pyrimidin-4-yl}-4-tert-butyl-benzenesulfonamide収率 91.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 31374Dimethylacetamide溶媒

実験手順

To a suspension of sodium hydride (0.25 g) in tetrahydrofuran (5 ml) is added dropwise a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (1.00 g) in dimethylacetamide (3 ml) and tetrahydrofuran (10 ml) at room temperature, and thereto is added 2-chloro-5-bromopyrimidine (0.56 g), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is acidified with ice-cold diluted hydrochloric acid, and extracted with ethyl acetate. The extract is washed, dried, and evaporated to remove the solvent. The resulting oily product is purified by silica gel column chromatography (solvent; chloroform), and crystallized from n-hexane to give 4-tert-butyl-N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (1.21 g) as crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe resulting oily product is purified by silica gel column chromatography (solvent; chloroform)
  7. customcrystallized from n-hexane

出典と根拠

ORDレコード
ord-f0bfe7cb12de4449ad46b88945212348
出典データセット
uspto-grants-1998_03
特許番号
US05728706

関連ノート

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