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

HRID 1271030

반응식

HRID 1271030 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac778f941d194820b478c15d66105573
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205297B2

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