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

HRID 1890660노트

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HRID 1890660 반응식
[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

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 23156191HCID 23156191, 화합물HCID 86583787Diisobutylaluminumhydride toluene

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a77ae37e2c544395ab70684d61b6495e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507484B2

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