7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → 4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1690040노트

반응식

HRID 1690040 반응식
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:11]1([Mg]Br)[CH2:13][CH2:12]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[CH:11]1([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:13][CH2:12]1

참가 물질

5

반응물 2

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 178418630HCID 178418630, 화합물

생성물 1

HCID 579633004-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine수율 99.4%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 0.452 g, 2.94 mmol), cyclopropylmagnesium bromide (43, 31.4 mL, 0.50 M in tetrahydrofuran, 15.7 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.240 g, complex 1:1 with dichloromethane, 0.294 mmol) were mixed with 15.4 mL of toluene. The reaction was heated at 60° C. overnight, then quenched with 1 M aqueous hydrochoric acid to pH 4 and filtered through a bed of celite. The layers of the filtrate were separated and the aqueous layer extracted with ethyl acetate: The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (44, 0.465 g). MS (ESI) [M+H+]+=160.1.

후처리

  1. customquenched with 1 M aqueous hydrochoric acid to pH 4
  2. filtrationfiltered through a bed of celite
  3. customThe layers of the filtrate were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum
  9. customThe resulting material was purified by silica gel column chromatography
  10. washeluting with ethyl acetate and hexane
  11. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-54f04cdc39c34f5baa80dc7d1ace052e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153641B2

반응 노트

불러오는 중…