Methyl iodide → HCID 66581031, compound

HRID 1521825Notes

Reaction equation

HRID 1521825 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([N:8]2[C:12]3[C:13]4[CH:19]=[CH:18][S:17][C:14]=4[S:15][CH2:16][C:11]=3[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:9]2)[CH:4]=[CH:3]1.[OH-].[Na+].[CH3:27]I>O.C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:27][N:7]1[C:2](=[O:1])[CH:3]=[CH:4][C:5]([N:8]2[C:12]3[C:13]4[CH:19]=[CH:18][S:17][C:14]=4[S:15][CH2:16][C:11]=3[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:9]2)=[CH:6]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 66578627HCID 66578627, compound

Product 1

HCID 66581031HCID 66581031, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of ethyl 1-(6-oxo-1,6-dihydropyridin-3-yl)-1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3-c]pyrazole-3-carboxylate (75 mg, 0.208 mmol) in water/DCM (1:2) is added tetrabutylammonium bromide (0.135 g, 0.417 mmol), sodium hydroxide (17 mg, 0.417 mmol) and methyl iodide (0.13 mL, 2.08 mmol). The reaction mass is stirred at RT for 12 h after which reaction mixture is diluted with DCM and washed with water. The organic layer is separated, dried over Na2SO4, concentrated under reduced pressure and purified by silica gel column chromatography over (5% MeOH in DCM) to afford the title compound. MS (ESI+): 374.0.

Workup

  1. customafter which reaction mixture
  2. washwashed with water
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography over (5% MeOH in DCM)

Sources & evidence

ORD record
ord-3b2446f3818c448b9db8f3380e947bb7
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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