cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene → Bicyclo[1.1.1]pent-1-yl-[2-chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-amine

HRID 82299노트

반응식

HRID 82299 반응식
[C:1]12([NH:6][C:7]3[C:12](Br)=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[CH2:15]([O:17]/[CH:18]=[CH:19]\[Sn](CCCC)(CCCC)CCCC)[CH3:16]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]12([NH:6][C:7]3[C:12](/[CH:16]=[CH:15]\[O:17][CH2:18][CH3:19])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2

참가 물질

5

반응물 2

HCID 5706773cis-1-Ethoxy-2-(tri-n-butylstannyl)ethyleneHCID 86672128Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine

생성물 1

HCID 86672129Bicyclo[1.1.1]pent-1-yl-[2-chloro-5-((Z)-2-ethoxy-vinyl)-pyrimidin-4-yl]-amine수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

To a stirred solution of Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine (Preparation 280, 2 g, 7.29 mmol) in dry toluene (70 mL) was added (Z)-1-ethoxy-2-(tributylstannyl)ethene (2.7 mL, 8.03 mmol). The reaction mixture was purged with N2 for min and then Pd(PPh3)4 (421 mg, 0.36 mmol) was added, followed by degassing for another 20 min and heating to 110° C. under N2 overnight. The reaction was cooled to room temperature, quenched with a 2M solution of KF and filtered through a pad of Celite. The filtrate was partitioned between water (50 mL) and EtOAc (200 mL). The organic phase was washed with brine (2×25 mL), dried (Na2SO4) and evaporated in vacuo. The crude residue was purified by column chromatography on silica gel (EtOAc: Hexane 18: 82) to afford the title compound as a pale green solid in 77% yield, 1.5 g.

후처리

  1. customThe reaction mixture was purged with N2 for min
  2. customby degassing for another 20 min
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with a 2M solution of KF
  5. filtrationfiltered through a pad of Celite
  6. customThe filtrate was partitioned between water (50 mL) and EtOAc (200 mL)
  7. washThe organic phase was washed with brine (2×25 mL)
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe crude residue was purified by column chromatography on silica gel (EtOAc: Hexane 18: 82)

출처 및 근거

ORD 기록
ord-a04855d6f4ad43a887dff7040ec05b64
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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