Potassium Carbonate → 2-[3-Chloro-2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6dimethoxypyrimidine

HRID 1885962Notes

Reaction equation

HRID 1885962 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]C2C=CC([N+]([O-])=O)=CC=2)=O)=[C:6]([O:20][C:21]2[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:31][CH:32]([S:34]([NH2:37])(=[O:36])=[O:35])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([NH:37][S:34]([CH:32]([CH3:33])[CH3:31])(=[O:36])=[O:35])=[O:10])=[C:6]([CH:5]=[CH:4][CH:3]=1)[O:20][C:21]1[N:22]=[C:23]([O:29][CH3:30])[CH:24]=[C:25]([O:27][CH3:28])[N:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3549191Propane-2-sulfonamideHCID 198765994-Nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate

Product 1

HCID 198765862-[3-Chloro-2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6dimethoxypyrimidineYield 38.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 0.43 grams (0.001 mole) of 4-nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate (prepared in Steps F and G), 0.12 gram (0.001 mole) of 1-methylethylsulfonamide, and 0.14 gram (0.001 mole) of potassium carbonate in 5 mL of acetonitrile was heated at reflux for five hours. The reaction mixture was then cooled and concentrated under reduced pressure to a residue. The residue was stirred with ethyl acetate and water, and the aqueous layer was separated. The aqueous layer was acidified with aqueous dilute hydrochloric acid and then was extracted with ethyl acetate. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was crystallized from diethyl ether. The solid was collected by filtration to yield 0.16 gram of 2-[3-chloro-2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6dimethoxypyrimidine; m.p. 150°-152° C., Compound 10 in Table 1. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for five hours
  2. temperatureThe reaction mixture was then cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. customthe aqueous layer was separated
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe extract was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was crystallized from diethyl ether
  10. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-8a40e02b40c04c6fa026dbbc767586c1
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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