Cesium fluoride → 2-Cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine

HRID 633732노트

반응식

HRID 633732 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC.[F-].[Cs+]>O1CCOCC1.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>[CH:10]1([CH2:9][O:8][C:5]2[N:4]=[CH:3][C:2]([C:18]([O:20][CH2:21][CH3:22])=[CH2:19])=[CH:7][N:6]=2)[CH2:12][CH2:11]1

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 638684135-Bromo-2-(cyclopropylmethoxy)pyrimidine

생성물 1

HCID 1181998532-Cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine수율 65.6%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

760 mg (3.32 mmol) of 5-bromo-2-cyclopropylmethoxypyrimidine in 15 mL of dioxane, 1.36 mL (3.82 mmol) of tributyl(1-ethoxyvinyl)tin, 58.22 mg (0.08 mmol) of bis(triphenylphosphine)palladium(II) chloride, 1.12 g (7.30 mmol) of cesium fluoride. This mixture is subjected to microwave irradiation at 110° C. for 1 hour. The reaction mixture is evaporated to dryness and the residue is taken up in 100 mL of ethyl ether. A solution of 2.80 g of cesium fluoride in 10 mL of water is added. After stirring for 1 hour at room temperature, the mixture is filtered through Celite. The filtrate is washed with aqueous NaHCO3 solution and then with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane) to give 480 mg of 2-cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine, the characteristics of which are as follows:

후처리

  1. customirradiation at 110° C. for 1 hour
  2. customThe reaction mixture is evaporated to dryness
  3. additionA solution of 2.80 g of cesium fluoride in 10 mL of water is added
  4. filtrationthe mixture is filtered through Celite
  5. washThe filtrate is washed with aqueous NaHCO3 solution
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane)

출처 및 근거

ORD 기록
ord-e7ce809c36014d278ad07d9a7afe81da
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321790B2

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