Methyl iodide → HCID 57786055, compound

HRID 1399074Notes

Reaction equation

HRID 1399074 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=4[Cl:25])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:26]([OH:30])[CH2:27][CH2:28][CH3:29])=[CH:6][CH:5]=1.[CH3:31]I>CN(C)C=O.O>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=4[Cl:25])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:26]([O:30][CH3:31])[CH2:27][CH2:28][CH3:29])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57786226HCID 57786226, compound

Product 1

HCID 57786055HCID 57786055, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 7.6 mg, 0.190 mmol) was added to a stirred solution of 1-[9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]butan-1-ol (69.5 mg, 0.158 mmol) in N,N-dimethylformamide (1.0 mL) at room temperature. After stirring 5 min, methyl iodide (33.6 mg, 0.237 mmol) was added to the mixture, and the mixture was stirred at room temperature for 3 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 5-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/diisopropyl ether to give the title compound as a colorless crystal (43.4 mg, 0.0958 mmol, 61%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 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 5-50% 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/diisopropyl ether

Sources & evidence

ORD record
ord-a43f7733878c48c6a9ac5564d817c8cc
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…