Hydrochloric Acid → 7-tert-Butyl-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 82168

반응식

HRID 82168 반응식
Cl.[C:2]([NH:6][C:7]1[C:12](/[CH:13]=[CH:14]/OCC)=[CH:11][N:10]=[C:9]([Cl:18])[N:8]=1)([CH3:5])([CH3:4])[CH3:3]>C(O)(C)C>[C:2]([N:6]1[C:7]2[N:8]=[C:9]([Cl:18])[N:10]=[CH:11][C:12]=2[CH:13]=[CH:14]1)([CH3:5])([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86672092N-tert-Butyl-2-chloro-5-[(E)-2-ethoxyvinyl]pyrimidin-4-amine

생성물 1

HCID 866720937-tert-Butyl-2-chloro-7H-pyrrolo[2,3-d]pyrimidine수율 85%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Concentrated HCl (25 mL) was added to N-tert-butyl-2-chloro-5-[(E)-2-ethoxyvinyl]pyrimidin-4-amine (5.3 g, 20.72 mmol) (see Preparation 61) in isopropanol (210 mL) and the mixture was heated at reflux for 4 hours. The reaction mixture was then evaporated in vacuo and the residue was basified with saturated aqueous NaHCO3 and extracted with EtOAc (200 mL). The organic extract was dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (gradient of hexane:EtOAc 93:7 to 90:10) to afford the title compound as a yellow oil in 85% yield, 3.7 g.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe reaction mixture was then evaporated in vacuo
  4. extractionextracted with EtOAc (200 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (gradient of hexane:EtOAc 93:7 to 90:10)

출처 및 근거

ORD 기록
ord-7004ab5fe70c4cd9bfd192617490c53f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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