Water → HCID 86595762、化合物

HRID 584789

反応式

HRID 584789 の反応式
[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[N:15]=[C:16]([CH3:19])[C:17](I)=[C:12]3[N:11]=[C:10]([CH3:20])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2].C[Si]([C:25]#[CH:26])(C)C.[F-].C[N+](C)(C)C.O>C(N(CC)CC)C.O1CCCC1.C(OCC)(=O)C.[Cu]I>[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[N:15]=[C:16]([CH3:19])[C:17]([C:25]#[CH:26])=[C:12]3[N:11]=[C:10]([CH3:20])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2]

参加物

9

反応物 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 67803Tetramethylammonium fluorideHCID 22249760HCID 22249760、化合物

生成物 1

HCID 86595762HCID 86595762、化合物収率 48.7%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 8-(1-ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (2.0 g, 5.29 mmol), trimethylsilylacetylene (0.8 mL, 5.82 mmol), Cl2Pd(PPh3)2 (0.19 g, 0.26 mmol) and copper(I) iodide (50 mg, 0.26 mmol) in triethylamine (20 mL) was stirred at room temperature for two hours. The solution was filtered through Celite, and the filtrate was evaporated. Tetramethylammonium fluoride (1.0 M tetrahydrofuran solution 6.3 mL, 6.3 mmol) was added to a solution of the residue in tetrahydrofuran (20 mL) at room temperature, followed by stirring for 10 minutes. Water was added thereto, and the mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane), to give the title compound (727 mg) as pale brown crystals.

後処理

  1. filtrationThe solution was filtered through Celite
  2. customthe filtrate was evaporated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-19220f35d51b456db0176c70c05bcd77
出典データセット
uspto-grants-2005_08
特許番号
US06927221B2

関連ノート

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