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

HRID 965630노트

반응식

HRID 965630 반응식
[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]([CH:17]=[CH: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]([CH:17]=[CH: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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 695584832-Phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

생성물 1

HCID 740471912-Phenyl-ethenesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide수율 19.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To sodium hydride (26 mg, 55-65% in mineral oil) was added THF (10 ml) followed by the addition of 2-phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (100 mg). The mixture was stirred for 1 h at rt. Then 2-chloro-pyrimidine (46 mg) was added and stirring continued for 19 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 and acidified by citric acid. The precipitate was filtered off and the crude material was purified by chromatography over silicagel with hexane/EtOAc=1/1 to give 2-phenyl-ethenesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (23.7 mg); tR=4.85 (LC); [M+H]+=490.27 (ES+).

후처리

  1. stirringstirring
  2. waitcontinued for 19 h at 80° C
  3. customThe solvent was evaporated
  4. additiondiethylether (20 ml) was added to the residue
  5. filtrationThe precipitate was filtered off
  6. washwashed with diethylether
  7. dissolutiondissolved in water
  8. filtrationThe precipitate was filtered off
  9. customthe crude material was purified by chromatography over silicagel with hexane/EtOAc=1/1

출처 및 근거

ORD 기록
ord-677146c2cf324916b5d60831259476d8
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951856B2

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