Dimethyl Sulfate → HCID 67654223, compound

HRID 2393337Notes

Reaction equation

HRID 2393337 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]([CH2:20][C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[N:16]=2)[N:3]=1.[H-].[Na+].C(CNC[CH:36]=[O:37])=O.[CH3:38]OS(OC)(=O)=O>CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](=[CH:38][O:37][CH3:36])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([CH2:20][C:21]3[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=3[Cl:27])[N:16]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18975622HCID 18975622, compoundHCID 202686642,2'-Azanediyldiacetaldehyde

Product 1

HCID 67654223HCID 67654223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The intermediate methyl 2-[2,4-dimethyl-6-(1-(2,6-dichlorobenzyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-acetate (9,6 g, 23 mmol) is dissolved in dimethylformamide (20 ml) and added at +30° C. to a suspension of NaH (1.3 g, of a 80% suspension in oil, 46 mmol) and N,N-diformylmethylamine (10 ml) in dimethylformamide (40 ml). The mixture is stirred for 2 hours at +45° C. Dimethylsulfate (2,4 ml, 25 mmol) is added at room temperature with cooling and stirring is continued for additional two hours. Dilution with ether, washing with brine, drying and chromatography on silicagel (eluant:ethyl acetate/hexane 3:1) gives methyl 2-[2,4-dimethyl-6-(1-(2,6-dichlorobenzyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-3-methoxyacrylate as a colorless oil (4.8 g).

Workup

  1. temperaturewith cooling
  2. stirringstirring
  3. waitis continued for additional two hours
  4. washDilution with ether, washing with brine
  5. customdrying

Sources & evidence

ORD record
ord-e5c050b72b1d4ead92fe495ed094dc2a
Source dataset
uspto-grants-1998_09
Patent number
US05807863

Reaction notes

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