Dimethyl Sulfate → 2,4(1H,3H)-Pyrimidinedione, 3-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-1,6-dimethyl-

HRID 1722942노트

반응식

HRID 1722942 반응식
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[O:23])[NH:14]/[C:15](/[CH3:22])=[CH:16]\[C:17]([O:19]CC)=O)=[C:4]([F:24])[CH:3]=1.[H-].[Na+].S(OC)(O[CH3:31])(=O)=O>CN(C)C=O.C(O)(C)C.CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([N:12]2[C:17](=[O:19])[CH:16]=[C:15]([CH3:22])[N:14]([CH3:31])[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 70395142HCID 70395142, 화합물

생성물 1

HCID 1354002,4(1H,3H)-Pyrimidinedione, 3-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-1,6-dimethyl-

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 20197112Isopropanol dimethylformamide용매

실험 절차

A solution of 9.00 g of ethyl 3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-crotonate in 100 ml of anhydrous dimethylformamide is added dropwise at room temperature while stirring to a solution of 1.10 g of a 55% sodium hydride dispersion in 100 ml of isopropanol/dimethylformamide (1:1) and stirred for 1 hour. The reaction mixture is subsequently treated with 4.70 g of dimethYl sulphate and stirred at room temperature for 2 hours. The solvent is largely distilled off under reduced pressure and the residue is poured into 500 ml of water and extracted twice with 200 ml of ethyl acetate each time. The organic phases are washed with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from diethyl ether/n-hexane. There is obtained 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1,6 -dimethyl-2,4(1H,3H)-pyrimidinedione, m.p. 149°-151° C.

후처리

  1. stirringstirred at room temperature for 2 hours
  2. distillationThe solvent is largely distilled off under reduced pressure
  3. additionthe residue is poured into 500 ml of water
  4. extractionextracted twice with 200 ml of ethyl acetate each time
  5. washThe organic phases are washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue is recrystallized from diethyl ether/n-hexane

출처 및 근거

ORD 기록
ord-db7a21edb72740e2bfdd87acee9c9830
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04859229

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