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

HRID 12711Notes

Reaction equation

HRID 12711 reaction equation
[I:1][C:2]1[C:3](=[O:36])[N:4](C(C2C=CC=CC=2)=O)[C:5](=[O:27])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH:15]3[C:13]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)([CH2:14]3)[CH2:12]2)[CH:7]=1.CO>N>[I:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:27])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH:15]3[C:13]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)([CH2:14]3)[CH2:12]2)[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 691348525-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 691341435-iodo-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedioneYield 81%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

(1R,5S/1S,5R) 5-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione (Prep82, 250 mg, 0.410 mmol) was dissolved in 3% ammonia in MeOH, (4 mL, 5.55 mmol). The mixture was stirred at room temperature for 3 hours, the solvent was then evaporated under vacuum and the crude purified by SPE Si (20 g) with Toluene/acetone 80/20 to give a solid that was then loaded through a SCX (5 g) cartridge in order to recover the title compound (168 mg, 0.332 mmol, 81% yield) as a white solid.

Workup

  1. customthe solvent was then evaporated under vacuum
  2. customthe crude purified by SPE Si (20 g) with Toluene/acetone 80/20
  3. customto give a solid

Sources & evidence

ORD record
ord-081bd455c8474bb09558117224f90bfc
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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