Methyl iodide → HCID 57786015, compound

HRID 1628765Notes

Reaction equation

HRID 1628765 reaction equation
[H-].[Na+].[CH:3]1([CH:6]([C:8]2[C:13]3[N:14]4[CH2:20][CH2:19][CH2:18][N:17]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])[C:15]4=[N:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)[OH:7])[CH2:5][CH2:4]1.[CH3:29]I>CN(C)C=O.O>[CH:3]1([CH:6]([O:7][CH3:29])[C:8]2[C:13]3[N:14]4[CH2:20][CH2:19][CH2:18][N:17]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])[C:15]4=[N:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57785945HCID 57785945, compound

Product 1

HCID 57786015HCID 57786015, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 45.3 mg, 1.13 mmol) was added to a stirred solution of cyclopropyl[1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (400 mg, 1.03 mmol) in N,N-dimethylformamide (3.0 mL) at 0° C. After stirring 5 min, methyl iodide (219 mg, 1.55 mmol) was added to the mixture, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with water, 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 purified by flash column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless crystal (265 mg, 0.659 mmol, 64%).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-209e4318a4ef401b9744f4690e712aef
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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