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

HRID 1893760ノート

反応式

HRID 1893760 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-223a041849244f3c9d634b4ea6e186f9
出典データセット
uspto-grants-2013_08
特許番号
US08513263B2

反応ノート

読み込み中…