Sodium Iodide → HCID 178433501, compound

HRID 1399130Notes

Reaction equation

HRID 1399130 reaction equation
I[Si](C)(C)C.[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:21]([CH3:29])=[N:22][C:23]([O:27]C)=[N:24][C:25]=4[CH3:26])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH:30]([O:35][CH:36]([F:38])[F:37])[C:31]([F:34])([F:33])[F:32])=[CH:9][CH:8]=1.[I-].[Na+]>C(#N)C.C(=O)([O-])O.[Na+]>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:21]([CH3:29])=[N:22][C:23]([OH:27])=[N:24][C:25]=4[CH3:26])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH:30]([O:35][CH:36]([F:37])[F:38])[C:31]([F:34])([F:33])[F:32])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 85247Trimethylsilyl iodideHCID 441296849-Chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Product 1

HCID 178433501HCID 178433501, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Iodo(trimethyl)silane (0.52 mL, 3.63 mmol) was added to a stirred mixture of 9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (595 mg, 1.21 mmol) and sodium iodide (544 mg, 363 mmol) in acetonitrile (8.0 mL) at room temperature, and the mixture was stirred at room temperature for 8 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethanol/ethyl acetate to give the title compound as a colorless crystal (366 mg, 0.766 mmol, 63%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-6837d2e4dfa144139219b807929b9e07
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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