Ethyl Acetate → (2-(Phenylamino)pyrimidin-5-yl)methanol
Reaktionsgleichung
[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]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
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%).
Aufarbeitung
- stirringby stirring vigorously at room temperature
- washThe mixture was sequentially washed with water and saturated brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-a77ae37e2c544395ab70684d61b6495e
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08507484B2
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