Triphenylphosphine → 4-Phenoxy-6-prop-1-yn-1-ylpyrimidin-5-amine

HRID 1787027노트

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HRID 1787027 반응식
I[C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1.[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=CC=C[CH:17]=1.[F-].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C.C[Si](C)(C)C#CC.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.[Cu]I>[O:9]([C:6]1[C:7]([NH2:8])=[C:2]([C:17]#[C:16][CH3:21])[N:3]=[CH:4][N:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

10

반응물 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 860847854-Iodo-6-phenoxy-5-pyrimidinamine

생성물 1

HCID 568510544-Phenoxy-6-prop-1-yn-1-ylpyrimidin-5-amine수율 730%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 803631-(Trimethylsilyl)prop-1-yne용매

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온도
60 °C

실험 절차

4-Iodo-6-phenoxypyrimidin-5-amine (5.00 g) was dissolved in a mixed solvent of N,N-dimethylformamide (100 mL)/triethylamine (50 mL), and 1-(trimethylsilyl)-1-propyne (3.3 mL), trans-dichlorobis(triphenylphosphine)palladium(II) (557.7 mg), triphenylphosphine (421.1 mg), copper(I) iodide (303.0 mg) and potassium fluoride (1.29 g) were sequentially added. The mixture was stirred at 60° C. under an argon stream for 16 hrs. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate solution and extracted with diethyl ether. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50) to give the title compound (2.64 g) as a orange solid.

후처리

  1. additionwere sequentially added
  2. extractionextracted with diethyl ether
  3. washThe organic layer washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50)

출처 및 근거

ORD 기록
ord-dac612e5b1094d8cb4d10e4b5dcb4f11
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507740B2

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