Sodium Methoxide → HCID 13784172, compound

HRID 570007Notes

Reaction equation

HRID 570007 reaction equation
[CH3:1][O-:2].[Na+].[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[C:21](Cl)[C:20]([C:24]([O:26][CH2:27]C)=[O:25])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH2:4]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[N:22]=[C:21]([O:2][CH3:1])[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][N:18]=2)[CH2:15][CH2:16]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13769893HCID 13769893, compound

Product 1

HCID 13784172HCID 13784172, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a methanol solution (50 ml) of 1.88 g (34.8 mmol) of sodium methoxide, a methanol solution (40 ml) of 10.1 g (28.0 mmol) of ethyl 2-(4-benzylpiperazino)-4-chloropyrimidine-5-carboxylate (the compound synthesized in Referential Example 63) was added dropwise over 10 minutes. The resultant mixture was stirred at room temperature for 1 hour. Methanol was distilled off under reduced pressure and water was added, followed by extraction with chloroform. After drying the chloroform layer with MgSO4, chloroform was distilled off under reduced pressure and the residue was recrystallized from methanol-ethyl acetate to obtain 7.9 g of the above-identified compound (yield: 79%).

Workup

  1. additionwas added dropwise over 10 minutes
  2. distillationMethanol was distilled off under reduced pressure and water
  3. additionwas added
  4. extractionfollowed by extraction with chloroform
  5. dry with materialAfter drying the chloroform layer with MgSO4, chloroform
  6. distillationwas distilled off under reduced pressure
  7. customthe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-4b96e9da954e4a33a076a6c9a572112a
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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