Citric Acid → Ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 2252722

反応式

HRID 2252722 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]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:6]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[H-].[Na+].Cl[C:27]1[N:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Br:33][C:30]1[CH:29]=[N:28][C:27]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])[C:6]=2[C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[N:32][CH:31]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 59645277Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

生成物 1

HCID 10311226Ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide収率 34.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (135 mg) was dissolved in THF (15 ml) and sodium hydride (80 mg) was added followed by stirring for 15 min at 50° C. Then 2-chloro-5-bromo-pyrimidine (162 mg) was added and stirring was continued for 8 h at 70 C. The reaction mixture was poured onto ice water, acidified with solid citric acid and extracted with ethylacetate. The combined organic extracts were dried over magnesium sulfate and the solvent was evaporated. The crude material was purified by plate chromatography with ethyl acetate/hexane=½ to give ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (68 mg) as a white powder. LC-MS: tR: 4.64, [M+H]+: 496.19.

後処理

  1. stirringstirring
  2. waitwas continued for 8 h at 70 C
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe crude material was purified by plate chromatography with ethyl acetate/hexane=½

出典と根拠

ORDレコード
ord-655d6fd4792649d384053cec1d355535
出典データセット
uspto-grants-2008_01
特許番号
US07323465B2

関連ノート

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