Reaktion #318695

Reaktionsgleichung

phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

sodium cyanoborohydride

acetic

→

desired product

Phenyl[4,5,6,7-tetrahydro-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas also added
2. 2
   SonstigeAfter 3 hours the solution was evaporated to dryness in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
4. 4
   workup.ADDITIONtreated with saturated sodium bicarbonate until basic
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeEvaporation
8. 8
   Sonstigegave a gummy solid
9. 9
   SonstigeThe solid was recrystallized from isopropyl alcohol

Vorschrift

To a 20.0 g portion of phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone (prepared as described in Ex. 9) suspended and stirred in 100 ml of glacial acetic acid under nitrogen was added in portions 8.5 g of sodium cyanoborohydride, during this addition another 50 ml of glacial acetic was also added. After 3 hours the solution was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane and treated with saturated sodium bicarbonate until basic. The organic layer was separated and dried over anhydrous sodium sulfate. Evaporation gave a gummy solid. The solid was recrystallized from isopropyl alcohol and gave the desired product as a light yellow solid, mp 186°-189° C.

Quelle