Triethylamine → 4-chloro-5-trimethylsilylethynyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 2059575ノート

反応式

HRID 2059575 の反応式
[Al].[Cl:2][C:3]1[C:4]2[C:11](I)=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C1COCC1.[Cu]I.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.CN(C=O)C>[Cl:2][C:3]1[C:4]2[C:11]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 5359268AluminumHCID 148092816-Chloro-7-iodo-7-deazapurine

生成物 1

HCID 112996804-chloro-5-trimethylsilylethynyl-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a 250 ml round-bottomed flask, protected from light with aluminum foil, are added 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.3 g, 4.6 mmol), copper(I) iodide (0.17 g, 0.93 mmol), trimethylsilylacetylene (0.96 ml, 6.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.26 g, 0.23 mmol) dissolved in anhydrous THF (60 ml), anhydrous DMF (20 ml) and triethyl amine (0.64 ml, 4.65 mmol). The reaction mixture is stirred at room temperature under nitrogen for 16 hrs. The solvent is removed in vacuo, and the residue is dissolved in methylene chloride (250 ml). The reaction mixture is washed with water (3×50 ml), and the combined organic layer is dried over Na2SO4, and concentrated in vacuo. The crude residue is purified by flash-chromatography on silica gel and eluted with 70% EtOAc in cyclohexane. Fractions containing the desired product (TLC) are pooled and evaporated to afford 4-chloro-5-trimethylsilylethynyl-7H-pyrrolo[2,3-d]pyrimidine as a tan white solid.

後処理

  1. customTo a 250 ml round-bottomed flask, protected
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride (250 ml)
  4. washThe reaction mixture is washed with water (3×50 ml)
  5. dry with materialthe combined organic layer is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue is purified by flash-chromatography on silica gel
  8. washeluted with 70% EtOAc in cyclohexane
  9. additionFractions containing the desired product (TLC)
  10. customevaporated

出典と根拠

ORDレコード
ord-e44414f067384efcb9086dcad3c2f042
出典データセット
uspto-grants-2012_10
特許番号
US08278282B2

反応ノート

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