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Sodium hydride → 2-Phenyl-ethanesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 8616
ノート
印刷プレビュー

反応式

HRID 8616 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][S:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:16])=[O:15])[C:8]=1[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.Cl[C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1>C1COCC1>[N:34]1[CH:35]=[CH:36][CH:37]=[N:38][C:33]=1[O:3][CH2:4][CH2:5][O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][S:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:15])=[O:16])[C:8]=1[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=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

5

反応物 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 235482692-Phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

生成物 1

HCID 235482462-Phenyl-ethanesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide収率 74.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

To sodium hydride (50 mg, 60% in mineral oil) was added THF (25 ml) followed by 2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (150 mg, Referential Example 1). The mixture was stirred for 1 h at rt before 2-chloro-pyrimidine (86 mg) was added. Stirring was continued for 17 h at 80° C. The solvent was evaporated and diethylether (20 ml) was added to the residue. The precipitate was filtered off and washed with diethylether, dissolved in water (20 ml) and acidified with citric acid and extracted twice with EA (50 ml). The organic phase was washed with water, dried over Na2SO4 and evaporated. The residue is suspended in 2-propanol (15 ml) and stirred at 70° C. for 10 min and cooled to 0° C. before the solid material is collected, washed with 2-propanol (2 ml) and dried under high vacuum to furnish 2-phenyl-ethanesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (133 mg) as a white powder. LC-MS: tR=4.97 min, [M+1]+=492.34, [M−1]−=490.28.

後処理

  1. additionwas added
  2. customThe solvent was evaporated
  3. additiondiethylether (20 ml) was added to the residue
  4. filtrationThe precipitate was filtered off
  5. washwashed with diethylether
  6. dissolutiondissolved in water (20 ml)
  7. extractionextracted twice with EA (50 ml)
  8. washThe organic phase was washed with water
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. stirringstirred at 70° C. for 10 min
  12. customis collected
  13. washwashed with 2-propanol (2 ml)
  14. customdried under high vacuum

出典と根拠

ORDレコード
ord-d079313d911f414dad920cc4c299001d
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091201B2

反応ノート

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