Diisobutylaluminumhydride → HCID 68439304, Verbindung

HRID 2202420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202420
C([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[N:10][CH:11]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH3:23][C:7]1[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:8]=1

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 68439408HCID 68439408, Verbindung

Produkt 1

HCID 68439304HCID 68439304, VerbindungAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carboxylic acid ethyl ester (0.20 g, 0.63 mmol) in THF (6 mL) was added diisobutylaluminum hydride (1 M in hexanes; 1.25 mL, 1.25 mmol) dropwise. The mixture was warmed to rt over 1 h. The reaction was quenched with 1 M H2SO4 (2 mL). The mixture was neutralized with satd. aq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL), and satd. aq. sodium potassium tartrate (10 mL). The mixture was stirred vigourously until the layers separated. The organic layer was dried (Na2SO4) and concentrated to give the crude product (138 mg), which was used in the next step without further purification. 1H NMR (CDCl3): 8.07 (s, 1H), 4.52 (s, 2H), 3.42-3.33 (m, 2H), 2.88-2.74 (m, 2H), 2.41 (s, 3H), 2.23 (s, 3H), 1.93-1.83 (m, 2H), 1.72-1.53 (m, 4H), 1.35-1.16 (m, 5H).

Aufarbeitung

  1. customThe reaction was quenched with 1 M H2SO4 (2 mL)
  2. additionaq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL)
  3. customseparated
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-01b146b77fcd46d9b54b43c422ff334a
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365548B2

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