Dimethyl Sulfate → Acetate hexane

HRID 2393334Notes

Reaction equation

HRID 2393334 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1.[H-].[Na+].C(CNC[CH:33]=[O:34])=O.[CH3:35]OS(OC)(=O)=O>CN(C)C=O>[C:10]([O-:12])(=[O:11])[CH3:9].[CH3:24][CH2:25][CH2:20][CH2:21][CH2:22][CH3:23].[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](=[CH:35][O:34][CH3:33])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18975605HCID 18975605, compoundHCID 202686642,2'-Azanediyldiacetaldehyde

Product 2

HCID 22139250Acetate hexaneHCID 67655269HCID 67655269, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The intermediate methyl 2-[2,4-dimethyl-6-(1-phenyl-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-acetate (6.8 g, 20 mmol), NaH (0.8 g of a 80% suspension in oil, 25 mmol) and N,N-diformylmethylamine (5 ml) in dimethylformamide (40 ml) is stirred at 45° C. for two hours. Dimethylsulfate (2.4 ml, 25 mmol) is added at room temperature and stirring is continued for additional two hours. Dilution with ether, washing with brine, drying and chromatography on silicagel (eluant: ethyl, acetate/hexane 1:1) gives methyl 2-[2,4-dimethyl-6-(1-phenyl-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-3-methoxyacrylate as a colorless oil.

Workup

  1. washDilution with ether, washing with brine
  2. customdrying

Sources & evidence

ORD record
ord-e857cfefe4554d14a3e75cbf65ae5c4a
Source dataset
uspto-grants-1998_09
Patent number
US05807863

Reaction notes

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