Water → 5-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide

HRID 2085083

반응식

HRID 2085083 반응식
[K+].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH-:12])(=[O:11])=[O:10])=[N:7][CH:8]=1.[Cl:13][C:14]1[C:19]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[C:18](Cl)[N:17]=[C:16]([CH3:30])[N:15]=1.O>CS(C)=O>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:18]2[C:19]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:14]([Cl:13])[N:15]=[C:16]([CH3:30])[N:17]=2)(=[O:11])=[O:10])=[N:7][CH:8]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 219795994,6-Dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidineHCID 1317239925-Methyl-2-pyridine sulfonamide potassium salt

생성물 1

HCID 227293975-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide수율 76.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

At room temperature 2.95 g of 5-methyl-2-pyridine sulfonamide potassium salt (Example 3c) was added to a suspension of 2 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidine (Example 7b) in 30 ml DMSO. The mixture was stirred at room temperature for 48 h and was then poured onto 300 ml of water. The aqueous solution was extracted twice with 200 ml of diethyl ether. The organic layers were extracted with water and the aqueous layers were combined and acidified with 3 ml of acetic acid to pH 4. Precipitation of the product was enhanced by adding 100 ml of saturated aqueous sodium chloride and cooling the mixture to 0° C. Eventually, the precipitate was filtered off, washed with cold water and dried under high vacuum to give 2.26 g of 5-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide as a beige powder. LC-MS: tR=4.79 min, [M+1]+=421.42, [M−1]−=419.46.

후처리

  1. extractionThe aqueous solution was extracted twice with 200 ml of diethyl ether
  2. extractionThe organic layers were extracted with water
  3. customPrecipitation of the product
  4. additionby adding 100 ml of saturated aqueous sodium chloride
  5. temperaturecooling the mixture to 0° C
  6. filtrationEventually, the precipitate was filtered off
  7. washwashed with cold water
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-e4804a749a5c4e4f8d12564af1fd547c
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720322B2

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