Phenylacetylene → 4-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

HRID 1271030

反応式

HRID 1271030 の反応式
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[N:3]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cu](I)I.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.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[N:3]=1

参加物

6

反応物 2

HCID 10821PhenylacetyleneHCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

生成物 1

HCID 734464524-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 2.46 g 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine, 7.5 mL triethylamine, 0.064 g copper iodide, 0.12 g dichlorobis(triphenyl)phosphine palladium II and 0.9 mL phenylacetylene was stirred under nitrogen at room temperature for two days. The dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C. The residue was partitioned between dichloromethane and water. The organic phase was washed thrice with water, dried over sodium sulfate, filtered and evaporated to yield 3.37 g of a dark brown oil. The residue was dissolved in hexanes and purified by column chromatography on silica gel, eluting successively with hexanes, 1:1 dichloromethane/hexanes and dichloromethane. The product was obtained from the latter eluant to yield after evaporation, 1.69 (74%) g of 4-chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine.

後処理

  1. customThe dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C
  2. customThe residue was partitioned between dichloromethane and water
  3. washThe organic phase was washed thrice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ac778f941d194820b478c15d66105573
出典データセット
uspto-grants-2007_04
特許番号
US07205297B2

関連ノート

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