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Diethyl Ether → 7-(4'-Fluorophenyl)-6-hydroxymethyl-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidin

HRID 846593
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846593
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([CH3:17])[CH:16]=[C:12]3[N:11]=[C:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2[C:21](OCC)=[O:22])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+].C(OCC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]3[N:14]=[C:15]([CH3:17])[CH:16]=[C:12]3[N:11]=[C:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2[CH2:21][OH:22])=[CH:6][CH:7]=1
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Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 14994686Ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl)pyrazolo[1,5-a]pyrimidin-6-ylcarboxylateHCID 86583787Diisobutylaluminumhydride toluene

Produkt 1

HCID 149946877-(4'-Fluorophenyl)-6-hydroxymethyl-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidinAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.40 g (12.9 mmol) of ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidin-6-ylcarboxylate was dissolved in 40 ml of dry toluene under a nitrogen atmosphere and cooled to 0° C. in an ice bath. To this solution, 33 ml of a 16 weight % diisobutylaluminium hydride-toluene solution was dropwise added, and then, the mixture was stirred at 0° C. for one hour. After confirming the complete disappearance of ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl) pyrazolo[1,5-a]pyrimidin-6-ylcarboxylate by thin layer chromatography, a saturated ammonium chloride aqueous solution was added thereto at 0° C. to terminate the reaction. Diethyl ether was added to the reaction mixture, and the organic layer was separated. The gelled substance was dissolved by an addition of a sodium hydroxide aqueous solution and newly extracted with ethyl ether. The ethyl ether extracts were put together and dried over anhydrous magnesium sulfate. The extract was subjected to filtration, and the solvent was distilled off and the residue was recrystallized from ethyl acetate to obtain 3.24 g (yield: 84%) of the slightly yellow desired compound.

Aufarbeitung

  1. customat 0° C. to terminate
  2. customthe reaction
  3. customthe organic layer was separated
  4. dissolutionThe gelled substance was dissolved by an addition of a sodium hydroxide aqueous solution
  5. extractionnewly extracted with ethyl ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe extract was subjected to filtration
  8. distillationthe solvent was distilled off
  9. customthe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7c6be4a211d54445a890a98d33c97a10
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05137891

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