Dimethyl Sulfate → HCID 11431603, compound

HRID 902094Notes

Reaction equation

HRID 902094 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]2[N:22]3[C:17](=[CH:18][C:19]([CH3:23])=[N:20][C:21]=13)[N:16]([CH:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[C:15]2=[NH:31].[CH3:32]OS(OC)(=O)=O.[H-].[Na+].[OH-].[Na+]>O1CCCC1.O>[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]2[N:22]3[C:17](=[CH:18][C:19]([CH3:23])=[N:20][C:21]=13)[N:16]([CH:24]([CH2:25][CH2:26][CH3:27])[CH2:28][CH2:29][CH3:30])[C:15]2=[N:31][CH3:32]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 69314240HCID 69314240, compound

Product 1

HCID 11431603HCID 11431603, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 4-(2-bromo-4-isopropyl-phenyl)-6-methyl-1-(1-propyl-butyl)-1H-1,5,7b-triaza-cyclopenta[cd]inden-2-ylideneamine hydrochloride (350 mg) and dimethylsulfate (866 mg) in tetrahydrofuran (3.5 mL) was added NaH (60% in oil, 139 mg) and heated at 65° C. for 1 hour. After addition of water, the reaction mixture was poured into 2.5 M NaOH aqueous solution, extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform/ethyl acetate=10:1) to give [4-(2-bromo-4-isopropyl-phenyl)-6-methyl-1-(1-propyl-butyl)-1H-1,5,7b-triaza-cyclopenta[cd]inden-2-ylidene]-methyl-amine (135 mg)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-48283ab0a6b14a21a9a966c8645d8b88
Source dataset
uspto-grants-2008_04
Patent number
US07365078B2

Reaction notes

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