Reaktion #441370

Reaktionsgleichung

5-(5-Iodo-2-isobutoxy-3-pyridinyl)-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

triethylamine

carbon monoxide

N′-hydroxyethanimidamide

acetamidoxime

triethylamine

→

product

Ausbeute 39.4%

5-[2-Isobutoxy-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinyl]-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Ausbeute 39.4%

Lösungsmittel

toluene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooled reaction mixture
2. 2
   Waschenwashed with water and brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigePurification
7. 7
   Waschenby flash column chromatography (gradient elution from dichloromethane:1% methanol:dichloromethane)

Vorschrift

5-(5-Iodo-2-isobutoxy-3-pyridinyl)-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 22) (200 mg, 0.42 mmol) and N′-hydroxyethanimidamide (EP 795 328) (95 mg, 1.28 mmol) were suspended in toluene (4 mL) and triethylamine (86 mg, 0.85 mmol) was added. Pd(PPh3)2Cl2 (15 mg, 0.02 mmol) was added and placed in a preheated oil bath at 95° C. under 1 atmosphere carbon monoxide. After 4 h a further portion of acetamidoxime (50 mg), triethylamine (43 mg) and Pd(PPh3)2Cl2 (15 mg) were added and stirring was continued at 95° C. for 14 h. The cooled reaction mixture was diluted with ethyl acetate and washed with water and brine, dried (MgSO4), filtered and evaporated. Purification by flash column chromatography (gradient elution from dichloromethane:1% methanol:dichloromethane) gave 70 mg product.

Quelle