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

HRID 537752ノート

反応式

HRID 537752 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-6462f34f0abd4e22a11884576d49f285
出典データセット
uspto-grants-2014_10
特許番号
US08865698B2

反応ノート

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