1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-2-(2-furyl)-7-(4-(2-hydroxy-2-methylpropyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264874ノート

反応式

HRID 1264874 の反応式
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4](Cl)[N:3]=1.C1CCN2C(=NCCC2)CC1.[OH:28][C:29]([CH3:38])([CH3:37])[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CS(C)=O>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:34]2[CH2:35][CH2:36][N:31]([CH2:30][C:29]([OH:28])([CH3:37])[CH3:38])[CH2:32][CH2:33]2)[N:3]=1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2582022-Methyl-1-(piperazin-1-yl)propan-2-olHCID 99427675-Amino-7-chloro-2-(2-furyl)[1,2,4]triazolo[1,5-c]pyrimidine

生成物 1

HCID 154891855-Amino-2-(2-furyl)-7-(4-(2-hydroxy-2-methylpropyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine収率 33%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

Into 7 mL of DMSO, 500 mg (2.12 mmol) of Compound E was dissolved, and then 0.95 mL (6.36 mmol) of DBU and 1.50 g (9.50 mmol) of 1-(2-hydroxy-2-methylpropyl)piperazine were added thereto, followed by stirring at 140° C. for about 2 hours. After completion of the reaction, the reaction mixture was extracted by adding chloroform and water, and the organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography (3% methanol-chloroform) and then recrystallized from a mixed solvent of hexane-ethyl acetate to obtain 250 mg of Compound 1 as a white solid (yield: 33%).

後処理

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted
  3. additionby adding chloroform and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe resulting residue was purified by silica gel column chromatography (3% methanol-chloroform)
  8. customrecrystallized from a mixed solvent of hexane-ethyl acetate

出典と根拠

ORDレコード
ord-e2148aa9fbf54eeebc9d8a6054e8592c
出典データセット
uspto-grants-2003_04
特許番号
US06545000B1

反応ノート

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