Ethyl Acetate → (2-(Phenylamino)pyrimidin-5-yl)methanol

HRID 1890660ノート

反応式

HRID 1890660 の反応式
[C:1]1([NH:7][C:8]2[N:13]=[CH:12][C:11]([C:14](OCC)=[O:15])=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:15][CH2:14][C:11]1[CH:10]=[N:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH:12]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 23156191HCID 23156191、化合物HCID 86583787Diisobutylaluminumhydride toluene

生成物 1

HCID 23156172(2-(Phenylamino)pyrimidin-5-yl)methanol収率 79.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

Ethyl 2-(phenylamino)pyrimidine-5-carboxylate (0.590 g, 2.42 mmol) obtained in Step 2 was dissolved in toluene (25 mL). After cooling to −78° C., a 1 mol/L diisobutyl aluminum hydride-toluene solution (7.30 mL, 7.30 mmol) was added to the solution, followed by stirring at −78° C. for 3 hours. The reaction mixture was added with ethyl acetate followed by stirring vigorously at room temperature. The mixture was sequentially washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to obtain 5-hydroxymethyl-2-(phenylamino)pyrimidine (386 mg, 79%).

後処理

  1. stirringby stirring vigorously at room temperature
  2. washThe mixture was sequentially washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

出典と根拠

ORDレコード
ord-a77ae37e2c544395ab70684d61b6495e
出典データセット
uspto-grants-2013_08
特許番号
US08507484B2

反応ノート

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