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

HRID 2085083

反応式

HRID 2085083 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e4804a749a5c4e4f8d12564af1fd547c
出典データセット
uspto-grants-2004_04
特許番号
US06720322B2

関連ノート

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