3-Benzoyl-5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione → 5-iodo-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

HRID 12672Notes

Reaction equation

HRID 12672 reaction equation
C([N:9]1[C:14](=[O:15])[C:13]([I:16])=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][C@H:24]3[C@:22]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)([CH2:23]3)[CH2:21]2)[C:10]1=[O:36])(=O)C1C=CC=CC=1>N.CO>[I:16][C:13]1[C:14](=[O:15])[NH:9][C:10](=[O:36])[N:11]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][C@H:24]3[C@:22]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=4)([CH2:23]3)[CH2:21]2)[CH:12]=1

Participants

4

Reactant 1

HCID 675197023-Benzoyl-5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione

Product 1

HCID 675197195-iodo-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedioneYield 74%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

3-Benzoyl-5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione (Prep 39, 840 mg, 1.38 mmol) was dissolved in 10% NH3 in MeOH solution (5 mL). The mixture was stirred at room temperature for 1 hour, the solvent was then evaporated under vacuum and the crude purified by flash chromatography with DCM-MeOH—NH4OH (98-2-1) to give the title compound as a white solid (515 mg, 74% yield).

Workup

  1. customthe solvent was then evaporated under vacuum
  2. customthe crude purified by flash chromatography with DCM-MeOH—NH4OH (98-2-1)

Sources & evidence

ORD record
ord-e8ff280b1b2d40039c2c5cf79d7bd198
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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