HCID 71746453, Verbindung → 2-[1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 570547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570547
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:14]=[C:15](I)[C:16]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:17]=3[N:18]=2)=[N:6]1>CN(C=O)C.[Pd]>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:14]=[CH:15][C:16]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:17]=3[N:18]=2)=[N:6]1

Komponenten

4

Edukt 1

HCID 71746453HCID 71746453, Verbindung

Produkt 1

HCID 717464542-[1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-oneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

45 mg (0.08 mmol) of 2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were dissolved in 5 ml of absolute DMF, 18 mg (0.02 mmol) of 10% palladium on charcoal were added and hydrogenation was effected under standard hydrogen pressure overnight. The reaction mixture was filtered through Celite and concentrated, and the residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0). 25 mg of the target compound were obtained (80% of theory).

Aufarbeitung

  1. custompressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customthe residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0)

Quellen und Nachweise

ORD-Eintrag
ord-60a1f00ecfa546fea7854301f060aebc
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023849B2

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