Benzene, 1-chloro-4-ethynyl- → 4-Chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

HRID 1271031

반응식

HRID 1271031 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=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:26]#[C:25][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=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 70118Benzene, 1-chloro-4-ethynyl-HCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

생성물 1

HCID 734464494-Chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine수율 94.7%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of 0.722 g 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine, 3.5 mL triethylamine, 0.025 g copper iodide, 0.037 g dichlorobis(triphenyl)phosphine palladium II and 0.289 g 1-chloro-4-ethynylbenzene was stirred under nitrogen at room temperature for 18 hours. The dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C. The beige residue was partitioned between dichloromethane and water. The organic phase was washed twice with water, dried over sodium sulfate, filtered and evaporated to yield 1.0 g of a caramel colored film. The residue was dissolved in 1:1 dichloromethane/hexanes and purified by column chromatography on silica gel, eluting successively with 1:1 dichloromethane/hexanes, dichloromethane and ethyl acetate. The product was recovered from the latter two eluates by evaporation to yield 0.7 g of 4-chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine.

후처리

  1. customThe dark brown mixture was evaporated in vacuo at a bath temperature of 30–35° C
  2. customThe beige residue was partitioned between dichloromethane and water
  3. washThe organic phase was washed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield 1.0 g of a caramel colored film
  8. custompurified by column chromatography on silica gel
  9. washeluting successively with 1:1 dichloromethane/hexanes, dichloromethane and ethyl acetate
  10. customThe product was recovered from the latter two eluates by evaporation

출처 및 근거

ORD 기록
ord-5f70233f91a747e5ae1790c09c11c6e5
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205297B2

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