Toluene → 4-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

HRID 611531노트

반응식

HRID 611531 반응식
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(O)C>[Cl:1][C:2]1[C:3]2[C:10]([C:21]3[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=3)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 195974264-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 195974814-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
105 °C

실험 절차

A mixture of 4-chloro-5-iodo-7-isopropylpyrrolo[2,3-d]pyrimidine (0.57 g), 4-nitrophenylboronic acid (0.30 g), bis(triphenylphosphine)palladium (II) chloride (0.126 g), toluene (15 ml), ethanol (2 ml), water (4 ml) and sodium bicarbonate (0.45 g) was heated under nitrogen at 105° C. for 8 hours. The mixture was cooled to ambient temperature and then partitioned between brine (50 ml) and ethyl acetate (50 ml). The aqueous layer was further extracted with ethyl acetate and the combined ethyl acetate extracts were washed with water, dried, filtered and evaporated to leave a solid which was purified by flash column chromatography on silica using cyclohexane with increasing amounts of ethyl acetate as the mobile phase to give 4-chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between brine (50 ml) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined ethyl acetate extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid which
  9. customwas purified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-e4bd162e3c0b4c23a0239173e397c33f
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001839

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