1-Ethyl-4-ethynylbenzene → 4-Chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidine

HRID 1271039

반응식

HRID 1271039 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.[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=1)[CH3:19]>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.[Cu](I)I.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:19]#[C:18][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][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 1424251-Ethyl-4-ethynylbenzeneHCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

생성물 1

HCID 734464504-Chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidine수율 63.7%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of 6.3 g of 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine, 33 mL of triethylamine, 2.43 g of 4-ethyl-1-ethynylbenzene, 0.304 g of dichlorobis(triphenyl)phosphine palladium II and 0.21 g copper iodide was magnetically stirred at reflux temperature for 1.5 hrs. The mixture was filtered and the filtrate evaporated in vacuo. Both the precipitate and the evaporated filtrate were dissolved in dichloromethane and washed with water, dried over sodium sulfate, filtered and evaporated. The residues were dissolved in 1:1 dichloromethane-hexanes and separately purified by column chromatography. After initial elution with 1:1 dichloromethane-hexanes, the product was obtained by elution with dichloromethane and 50% ethyl acetate-dichloromethane. Evaporation of the eluates gave 4.04 g of 4-chloro-2-diisopropylaminomethyleneamino-5-(4-ethylphenylethynyl)pyrimidine as a thick amber syrup.

후처리

  1. temperatureat reflux temperature for 1.5 hrs
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. dissolutionBoth the precipitate and the evaporated filtrate were dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residues were dissolved in 1:1 dichloromethane-hexanes
  10. customseparately purified by column chromatography
  11. washAfter initial elution with 1:1 dichloromethane-hexanes
  12. customthe product was obtained by elution with dichloromethane and 50% ethyl acetate-dichloromethane
  13. customEvaporation of the eluates

출처 및 근거

ORD 기록
ord-00d218d8dd114839b00fe84d3161ce11
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205297B2

연결된 노트

불러오는 중…