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

HRID 82168

Reaction equation

HRID 82168 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7004ab5fe70c4cd9bfd192617490c53f
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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