N-Iodosuccinimide → 6-(4-fluoro-phenyl)-3-iodo-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538250Notes

Reaction equation

HRID 538250 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][C:19]3=[N:22][C:23]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:24][N:18]3[C:17]2=[O:33])=[CH:12][CH:11]=1>C(#N)C.C(O)(=O)C.C(Cl)Cl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][C:19]3=[N:22][C:23]([CH2:25][O:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:24]([I:1])[N:18]3[C:17]2=[O:33])=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 682902896-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

Product 1

HCID 682903836-(4-fluoro-phenyl)-3-iodo-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-oneYield 56%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N-iodosuccinimide (73.4 mg, 0.33 mmol) was added to a stirred solution of 6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (0.1 g, 0.3 mmol) in a mixture of ACN (2 mL) and acetic acid (2 mL). The mixture was stirred at RT for 3 days. The mixture was diluted with DCM and washed with a saturated solution of Na2CO3. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was triturated with MeOH to yield 6-(4-fluoro-phenyl)-3-iodo-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (46 mg, 56% yield) as a brown solid, that was used in the next step without further purification.

Workup

  1. washwashed with a saturated solution of Na2CO3
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was triturated with MeOH

Sources & evidence

ORD record
ord-ada2cdd0387045c9b0022bb32ae30772
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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