Sodium 2-(trifluoromethyl)benzene-1-sulfinate → 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidine

HRID 2353739ノート

反応式

HRID 2353739 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O-:11])=[O:10].[Na+].[Cl:15][C:16]1[N:21]=[C:20]([CH2:22]I)[CH:19]=[C:18]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])[N:17]=1>C(#N)C>[Cl:15][C:16]1[N:17]=[C:18]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])[CH:19]=[C:20]([CH2:22][S:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:12])[F:13])(=[O:11])=[O:10])[N:21]=1

参加物

4

反応物 2

HCID 23674774Sodium 2-(trifluoromethyl)benzene-1-sulfinate2 回HCID 59380103(S)-4-(2-Chloro-6-(iodomethyl)pyrimidin-4-YL)-3-methylmorpholine

生成物 1

HCID 593801482-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidine収率 59.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

Sodium 2-(trifluoromethyl)benzenesulfinate (10.24 g, 44 mmol) was added to 2-chloro-4-(iodomethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (13 g, 36.77 mmol), in acetonitrile (500 mL) at RT under nitrogen. The resulting mixture was stirred at 80° C. for 3 hours. Additional sodium 2-(trifluoromethyl)benzenesulfinate (10.2 g, 44 mmol) was added and reaction heated at 80° C. for 1 hour. The reaction mixture allowed to cool and concentrated in vacuo. The material was dissolved in ethyl acetate (500 mL), and washed with water (200 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane, to give the desired material as an orange/cream solid (9.48 g).

後処理

  1. customreaction
  2. temperatureheated at 80° C. for 1 hour
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutionThe material was dissolved in ethyl acetate (500 mL)
  6. washwashed with water (200 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto afford crude product
  11. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-e3ec402210e749e3954f5b2603ea11ba
出典データセット
uspto-grants-2010_07
特許番号
US07750003B2

反応ノート

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