1,4-Dioxane → 7-(2,4-Dichlorophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine

HRID 2389735ノート

反応式

HRID 2389735 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([S:15][CH2:16][CH3:17])[N:12]=[C:11]([NH2:18])[CH:10]=1.CO[CH:21](OC)[CH2:22]Br.O1CCOCC1>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([S:15][CH2:16][CH3:17])[N:12]2[CH:21]=[CH:22][N:18]=[C:11]2[CH:10]=1

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 816722-Bromo-1,1-dimethoxyethaneHCID 583060056-(2,4-Dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine

生成物 1

HCID 593131257-(2,4-Dichlorophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

48.5 g (161.55 mmol) of 6-(2,4-dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine (Example 3A) and 163.84 g (969.32 mmol) of bromoacetaldehyde dimethyl acetal are introduced into a mixture of 1164 ml of dioxane and 291 ml of water and heated under reflux for 16 h. The dioxane is substantially removed in vacuo, and 1000 ml of ethyl acetate and 1000 ml of saturated aqueous sodium bicarbonate solution are cautiously added. The phases are separated and a further extraction with ethyl acetate is carried out. The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and then freed of solvent. The residue is purified by silica gel chromatography. 16.6 g (27% of theory) of the product are obtained and are reacted further in this form.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. customThe dioxane is substantially removed in vacuo, and 1000 ml of ethyl acetate and 1000 ml of saturated aqueous sodium bicarbonate solution
  4. additionare cautiously added
  5. customThe phases are separated
  6. extractiona further extraction with ethyl acetate
  7. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customThe residue is purified by silica gel chromatography
  10. custom16.6 g (27% of theory) of the product are obtained
  11. customare reacted further in this form

出典と根拠

ORDレコード
ord-2e3dd8b2af1d4319a45ee0938e233ecd
出典データセット
uspto-grants-2012_09
特許番号
US08273752B2

反応ノート

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