Dimethyl Sulfate → HCID 18419445, compound

HRID 635012Notes

Reaction equation

HRID 635012 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=2)=[C:4]([CH3:16])[CH:3]=1.[OH-].[Na+].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH3:19])=[CH:9][N:8]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 28001436-(4-chloro-2-methylphenoxy)pyridin-3-amine

Product 1

HCID 18419445HCID 18419445, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
35 °C

Procedure

2-(4-Chloro-2-methyl-phenoxy)-5-aminopyridine (2.15 g, 9.16 mmol) was combined with powdered sodium hydroxide (1.46 g, 36.6 mmol), potassium carbonate (1.27 g, 9.16 mmol), tetrabutyl ammonium bromide (60 mg, 0.18 mmol) and toluene (10 mL) was stirred for 1 hour at 35° C. A solution of dimethyl sulfate (0.91 mL, 9.6 mmol) dissolved in toluene (5 mL) was added slowly. The mixture was heated at 35° C. for 20 hours. After cooling, the solids were removed by filtration and the solvent was concentrated in vacuo. The desired material was purified by chromatography on SiO2 using 30% ethyl acetate/hexanes as eluent. MS (m/z): 248/250 (M+H)+; C13H13N2OCl requires 249.

Workup

  1. additionwas added slowly
  2. temperatureThe mixture was heated at 35° C. for 20 hours
  3. temperatureAfter cooling
  4. customthe solids were removed by filtration
  5. concentrationthe solvent was concentrated in vacuo
  6. customThe desired material was purified by chromatography on SiO2 using 30% ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-059c95e8408e44e3a0fb87d96cf06bba
Source dataset
uspto-grants-2001_02
Patent number
US06184237B2

Reaction notes

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