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

HRID 1787027ノート

反応式

HRID 1787027 の反応式
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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 803631-(Trimethylsilyl)prop-1-yne溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dac612e5b1094d8cb4d10e4b5dcb4f11
出典データセット
uspto-grants-2009_03
特許番号
US07507740B2

反応ノート

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