N,N-Dimethylmethanesulphonamide → C-[3-(2-Chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide

HRID 230192

反応式

HRID 230192 の反応式
[CH3:1][N:2]([CH3:7])[S:3]([CH3:6])(=[O:5])=[O:4].[Li]CCCC.Cl[C:14]1[N:19]=[C:18]([S:20][CH3:21])[N:17]=[C:16]2[N:22]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[N:23]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[C:15]=12>C1COCC1>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]1[C:15]2[C:16](=[N:17][C:18]([S:20][CH3:21])=[N:19][C:14]=2[CH2:6][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])[N:22]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[N:23]=1

参加物

5

反応物 3

HCID 70191N,N-DimethylmethanesulphonamideHCID 578933704-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 68878703C-[3-(2-Chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide収率 70.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of N,N-dimethyl methanesulfonamide (419 mg, 3.40 mmol) in 5 mL dry THF at 5° C. was added n-BuLi (2.2 mL of 1.6M solution in hexanes 3.50 mmol) dropwise. To this stirring solution was added dropwise a solution of 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (0.500 g, 1.13 mmol) in 1 mL dry THF. The reaction mixture was stirred for 2 hours and allowed to warm to room temperature during this time. The reaction was quenched by addition of 10 mL water and 1 mL of 1.2M HCl, and the resulting aqueous solution was extracted twice w2ith 20 mL methylene chloride. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (0% to 30% EtOAc in hexanes) to give 421 mg of C-[3-(2-Chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide.

後処理

  1. customThe reaction was quenched by addition of 10 mL water and 1 mL of 1.2M HCl
  2. extractionthe resulting aqueous solution was extracted twice w2ith 20 mL methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (0% to 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-3382f6930c6e4b7e9511e46ef8a0e04a
出典データセット
uspto-grants-2009_07
特許番号
US07566708B2

関連ノート

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