Potassium Carbonate → HCID 15548995, compound

HRID 1954837Notes

Reaction equation

HRID 1954837 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:22]([CH3:25])([CH3:24])[OH:23])[CH:5]=[C:6]([O:20][CH3:21])[C:7]=1[O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[N:12]=[C:11]([CH3:19])[N:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][CH2:33][CH2:34][CH:35]([NH2:39])[CH2:36][CH2:37][CH3:38]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:22]([CH3:25])([CH3:24])[OH:23])[CH:5]=[C:6]([O:20][CH3:21])[C:7]=1[O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:39][CH:35]([CH2:36][CH2:37][CH3:38])[CH2:34][CH2:33][CH3:32])[N:12]=[C:11]([CH3:19])[N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 386654-HeptanamineHCID 21186062HCID 21186062, compound

Product 1

HCID 15548995HCID 15548995, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-5-methoxy-α,α-dimethyl-4-[[6-chloro-2-methyl-5-nitro-4-pyrimidinyl]oxy]benzenemethanol (1.88 g) in anhydrous 1,4-dioxane (50 mL) with 0.50 g of potassium carbonate, 4-heptylamine (1.00 mL) was added and the solution was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was taken up in water and extracted with methylene chloride. The extracts were combined and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using a 1:1 mixture of ethyl acetate and hexane to yield the title compound, mp 138° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with methylene chloride
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography on silica gel using
  6. additiona 1:1 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-76e870ed14f4468ea6ebe6326b425b71
Source dataset
uspto-grants-2000_09
Patent number
US06124300

Reaction notes

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