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

HRID 12709

Reaction equation

HRID 12709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][N:10]([CH2:14][CH2:15][CH2:16][N:17]2[CH:22]=[C:21]([I:23])[C:20](=[O:24])[N:19](C(C4C=CC=CC=4)=O)[C:18]2=[O:33])[CH2:9]3)=[CH:4][CH:3]=1.CO>N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][N:10]([CH2:14][CH2:15][CH2:16][N:17]2[CH:22]=[C:21]([I:23])[C:20](=[O:24])[NH:19][C:18]2=[O:33])[CH2:9]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 866159461-{3-[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hex-3-yl]propyl}-5-iodo-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 866159471-{3-[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hex-3-yl]propyl}-5-iodo-2,4(1H,3H)-pyrimidinedioneYield 83.6%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

(1R,5S/1S,5R)-(1-{3-[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hex-3-yl]propyl}-5-iodo-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (Prep 80, 190 mg, 0.330 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 cartridge (20 g) eluting with Toluene/acetone 80/20 to give an oil that was then loaded through SCX (5 g) cartridge to recover the title compound (130 mg, 0.276 mmol, 4.97% yield) as a light yellow oil.

Workup

  1. customwas then evaporated under vacuum
  2. customthe crude purified by SPE Si cartridge (20 g)
  3. washeluting with Toluene/acetone 80/20
  4. customto give an oil that

Sources & evidence

ORD record
ord-748fbad2856e4ad48b9a9f0a0b0784a7
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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