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

HRID 2353739노트

반응식

HRID 2353739 반응식
[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

참가 물질

4

반응물 2

HCID 23674774Sodium 2-(trifluoromethyl)benzene-1-sulfinate2회HCID 59380103(S)-4-(2-Chloro-6-(iodomethyl)pyrimidin-4-YL)-3-methylmorpholine

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3ec402210e749e3954f5b2603ea11ba
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750003B2

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