Methanol → HCID 57786239, compound

HRID 1399247Notes

Reaction equation

HRID 1399247 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:23]([O:25][CH3:26])=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]21.[CH3:27][O-:28].[Na+].CO>[Cu]I.CN(C)C=O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[N:11]1[C:8]2=[N:9][C:10]3[C:6](=[C:5]([C:23]([O:25][CH3:26])=[O:24])[CH:4]=[CH:3][C:2]=3[O:28][CH3:27])[N:7]2[CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 57785916HCID 57785916, compound

Product 1

HCID 57786239HCID 57786239, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 9-bromo-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (200 mg, 0.439 mmol), sodium methoxide (237 mg, 4.39 mmol), copper(I) iodide (100 mg, 0.525 mmol), Methanol (1.8 mL) and N,N-dimethylformamide (2.6 mL) was stirred at 100° C. for 4 hr. The reaction was quenched by aqueous saturated ammonium chloride, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (54.4 mg, 0.134 mmol, 31%).

Workup

  1. customThe reaction was quenched by aqueous saturated ammonium chloride
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-ec4ddeb83e2840d48f3640a5d2e52054
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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