Acetaldehyde → 3-Cyclopropylmethyl-8-[4-(ethyl-amino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

HRID 720688

Reaktionsgleichung

Reaktionsgleichung von HRID 720688
[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:22])[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:6]2=[O:31])[CH2:3][CH2:2]1.[CH:32](=O)[CH3:33]>[Pd].O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:16]=[CH:17][C:18]([NH:21][CH2:32][CH3:33])=[CH:19][CH:20]=4)[NH:10][C:9]=3[C:8](=[O:22])[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:6]2=[O:31])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 177AcetaldehydeHCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

Produkt 1

HCID 218918193-Cyclopropylmethyl-8-[4-(ethyl-amino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dioneAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 10% palladium on carbon (0.10 g) in tetrahydrofuran (50 mL) was added 3-cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione (prepared as described in example 64, step 1) (0.21 g, 0.50 mmol) and acetaldehyde (72.6 μL, 1.3 mmol). The mixture was shaken under an atmosphere of hydrogen at 1 atmosphere pressure and ambient temperature for 3 days. The catalyst was removed by filtration through celite, washing the filter pad through with tetrahydrofuran and methanol. The combined filtrate was concentrated in vacuo and the residue purified by chromatography using silica eluted with 1:1 hexanes/ethyl acetate. Concentration of the appropriate fractions gave the product as a colorless solid (0.14 g, 62%). MS, m/z(M+H)=553.

Aufarbeitung

  1. customThe catalyst was removed by filtration through celite
  2. washwashing the filter pad through with tetrahydrofuran and methanol
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. customthe residue purified by chromatography
  5. washeluted with 1:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d7b4319582c34293b3c5c8e64c59603d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135475B2

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