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

HRID 965632ノート

反応式

HRID 965632 の反応式
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:14])=[O:13])[C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1.[H-].[Na+].CN(C=O)C.Cl[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][N:39]=1>C1COCC1>[C:26]1([CH3:29])[CH:27]=[CH:28][C:23]([C:6]2[C:7]([NH:11][S:12]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:13])=[O:14])=[N:8][CH:9]=[N:10][C:5]=2[O:4][CH2:3][CH2:2][O:1][C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][N:39]=2)=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 695584832-Phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

生成物 1

HCID 740471892-Phenyl-ethenesulfonic acid {5-p-tolyl-6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-amide収率 64.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (150 mg) was dissolved in THF (10 ml) and sodium hydride (45 mg; 55-65% in mineral oil) was added. The mixture was stirred for 15 min at rt., followed by the addition of DMF (2 ml) and 2-chloro-5-trifluoromethyl-pyridine (146 mg) and heating to 75° C. for 5 h. Then the reaction mixture was evaporated to dryness and water (15 ml) and citric acid was added. The precipitated product was filtered off, washed with water and dried. 2-Phenyl-ethenesulfonic acid {5-p-tolyl-6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-amide (130 mg) could be obtained as a white powder. tR=5.92 (LC); [M+H]+=557.38 (ES+).

後処理

  1. temperatureheating to 75° C. for 5 h
  2. customThen the reaction mixture was evaporated to dryness and water (15 ml) and citric acid
  3. additionwas added
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-58bd497ef48448ff8d617a2df9a523e0
出典データセット
uspto-grants-2005_10
特許番号
US06951856B2

反応ノート

読み込み中…