2-(4-(Benzyloxy)phenyl)-7-(2-nitrophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile → 7-(2-Aminophenyl)-2-(4-hydroxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64268
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:32]([C:33]#[N:34])=[C:18]3[N:19]=[CH:20][CH:21]=[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[N+:29]([O-])=O)[N:17]3[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C(Cl)Cl.[Pd]>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH:22]1[N:17]2[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:32]([C:33]#[N:34])=[C:18]2[NH:19][CH2:20][CH2:21]1

Komponenten

5

Edukt 1

HCID 1176683182-(4-(Benzyloxy)phenyl)-7-(2-nitrophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 1369280897-(2-Aminophenyl)-2-(4-hydroxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrileAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-(benzyloxy)phenyl)-7-(2-nitrophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (2 g, 4.47 mmol) in CH3OH (20 mL) and DCM (20 mL) was added 10% w/w Pd/C (300 mg). The mixture was stirred at RT under H2 for 16 hr. Filtered and purified by chromatography column on silica gel (elution with DCM/CH3OH) to afford 0.92 g (62%) of 7-(2-aminophenyl)-2-(4-hydroxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile as a yellow solid. MS (ESI, m/e) [M+1]+ 331.9.

Aufarbeitung

  1. filtrationFiltered
  2. custompurified by chromatography column on silica gel (elution with DCM/CH3OH)

Quellen und Nachweise

ORD-Eintrag
ord-4a6284adca83431c8acee971e997d1ae
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

Notizen zur Reaktion

Wird geladen…