Sodium Methoxide → HCID 21182511, compound

HRID 1386617Notes

Reaction equation

HRID 1386617 reaction equation
CN([CH:4]=[CH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16]C)=[O:14])=[CH:9][CH:8]=1)C.Cl.[CH2:20]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[NH:32])=[CH:29][CH:28]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C[O-].[Na+]>CO>[CH2:20]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]2[N:33]=[CH:4][CH:5]=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=3)[N:32]=2)=[CH:34][CH:35]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12238501p-n-Hexyloxybenzamidine hydrochlorideHCID 54211795HCID 54211795, compound

Product 1

HCID 21182511HCID 21182511, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 1-(N,N-dimethylamino)-2-(4-ethoxycarbonylbenzoyl)ethylene (0.742 g) and 4-n-hexyloxybenzamidine hydrochloride (0.847 g) in methanol (10 ml) was added 28% sodium methoxide in methanol (0.64 ml). The suspension was refluxed for 6 hours, and partitioned with ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give Methyl 4-[2-(4-n-hexyloxyphenyl)pyrimidin-6-yl]benzoate (0.61 g).

Workup

  1. temperatureThe suspension was refluxed for 6 hours
  2. custompartitioned with ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with acetonitrile
  7. filtrationcollected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6059b437672d4236be52109495d66445
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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