1-Butanol → (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine

HRID 63972노트

반응식

HRID 63972 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1.C(O)CCC.CCN(C(C)C)C(C)C>CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1

참가 물질

6

반응물 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 71762902-(2,5-Difluorophenyl)pyrrolidine, (R)-HCID 210717595-Chloropyrazolo(1,5-a)pyrimidine

생성물 1

HCID 67329909(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine수율 68%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

In a pressure reaction tube was added 5-chloropyrazolo[1,5-a]pyrimidine (4.2 g, 27 mmol), (R)-2-(2,5-difluorophenyl)pyrrolidine (Preparation A; 5.3 g, 29 mmol), anhydrous n-butanol (5 ml, 55 mmol), and DIEA (9.5 ml, 55 mmol). The yellowish suspension was sealed and heated in an oil bath (160° C.) overnight. The reaction was cooled to ambient temperature, diluted with EtOAc (250 mL), and filtered, rinsing the solid with EtOAc. The filtrate (330 mL) was washed with water (2×150 mL), brine (100 mL), concentrated, and purified by silica chromatography, eluting with 2:1 EtOAc/hexanes to give the product as a bright yellowish solid (5.6 g, 68% yield).

후처리

  1. customIn a pressure reaction tube
  2. customPreparation A
  3. customThe yellowish suspension was sealed
  4. temperatureThe reaction was cooled to ambient temperature
  5. filtrationfiltered
  6. washrinsing the solid with EtOAc
  7. washThe filtrate (330 mL) was washed with water (2×150 mL), brine (100 mL)
  8. concentrationconcentrated
  9. custompurified by silica chromatography
  10. washeluting with 2:1 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-f585e131793a4c13ac03bf68c03b509b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447104B2

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