Sodium Carbonate → (4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)amine

HRID 1095412노트

반응식

HRID 1095412 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([C:15]([S:18]([CH3:21])(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([C:15]([S:18]([CH3:21])(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=[C:2]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)[N:7]=1

참가 물질

9

반응물 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 593802202-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidine

생성물 1

HCID 59380004(4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)amine수율 67.6%

시약·촉매·용매 5

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

Dichlorobis(triphenylphosphine)palladium(II) (0.287 g, 0.41 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidine (2.73 g, 8.18 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.329 g, 10.63 mmol) and 2M aqueous sodium carbonate (15 mL, 29.44 mmol) in DMF (15 mL), DME (15 mL), ethanol (15 mL) and water (37.5 mL) at RT under nitrogen. The reaction was purged with nitrogen for 15 minutes and the resulting mixture was stirred at 80° C. for 3 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and washed sequentially twice with water (150 mL) and saturated brine (150 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product as a dark brown gum. The crude product was purified by flash silica chromatography, eluting with 0 to 20% ethyl acetate in DCM, to give the desired material as a white solid (2.16 g).

후처리

  1. customThe reaction was purged with nitrogen for 15 minutes
  2. additionThe reaction mixture was diluted with ethyl acetate (300 mL)
  3. washwashed sequentially twice with water (150 mL) and saturated brine (150 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product as a dark brown gum
  8. customThe crude product was purified by flash silica chromatography
  9. washeluting with 0 to 20% ethyl acetate in DCM

출처 및 근거

ORD 기록
ord-7ad6daf426a54a7d86c484e202968165
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138183B2

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