Tetrahydrofuran → HCID 66692936, Verbindung

HRID 472815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472815
[CH3:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:5]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=[C:4]2[N:3]=1.CC(C[AlH]CC(C)C)C.C1COCC1>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:5]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=[C:4]2[N:3]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 66693154Methyl 5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carboxylate

Produkt 1

HCID 66692936HCID 66692936, VerbindungAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carboxylate (800 mg, 2.238 mmol) in CH2Cl2 (50 mL) was added DIBAL-H, 1M in THF (6.72 mL, 6.72 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 h before being quenched with saturated NH4Cl solution. The aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (344 mg, 46.7%). 1H-NMR (500 MHz, CDCl3) δ ppm 1.61 (1H, t, J=5.0 Hz), 2.49 (3H, s), 2.78 (3H, s), 4.59 (2H, d, J=5.0 Hz), 6.88 (1H, s), 7.29-7.42 (5H, m), 7.56 (2H, d, J=8.2 Hz), 7.81-7.96 (2H, m).

Aufarbeitung

  1. custombefore being quenched with saturated NH4Cl solution
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f3142686c1334359912a373d46215581
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633200B2

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