Reaktion #40988

Reaktionsgleichung

3-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(2H)-pyrimidinyl]propanal

1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Sodiumtriacetoxyborohydride

→

title compound

Ausbeute 46.6%

5-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

Ausbeute 46.6%

Lösungsmittel

NaHCO3

DCE

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Extraktionextracted with DCM
3. 3
   SonstigeThe solvent was evaporated
4. 4
   Sonstigethe crude purified by silica SPE column (20 g)
5. 5
   Wascheneluting with acetone/toluene 20:80
6. 6
   SonstigeAfter evaporation

Vorschrift

To a solution of 3-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(2H)-pyrimidinyl]propanal (P38, 350 mg, 0.88 mmol) and (1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (racemate, reference procedure for preparation reported in WO2005/080382, 200 mg, 0.88 mmol) in dry DCE (10 ml), AcOH was added and the reaction mixture cooled to 0° C. Sodiumtriacetoxyborohydride (224 mg, 1.055 mmol) was added and the reaction left at 0° C. for 4 hrs. Reaction monitored by LC/MS. The mixture was diluted with a saturated solution of NaHCO3 and extracted with DCM. The solvent was evaporated and the crude purified by silica SPE column (20 g) eluting with acetone/toluene 20:80. After evaporation, 250 mg of the title compound were obtained.

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