Cyclopropylamine → HCID 58316743, compound

HRID 1396140Notes

Reaction equation

HRID 1396140 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:11]1([NH2:14])[CH2:13][CH2:12]1>O>[CH:11]1([NH:14][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 58316743HCID 58316743, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (9, 1.06 g, 6.90 mmol) is dissolved in cyclopropylamine (20, 2.42 mL, 34.5 mmol) and heated to reflux overnight. The reaction mixture is cooled and poured into water, then extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (21, 337 mg). MS (ESI) [M+H+]+=174.9. This is reacted similarly to step 2 of Scheme 4 to provide the desired compound 22.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum
  9. customThe resulting material is purified by silica gel column chromatography
  10. washeluting with ethyl acetate and dichloromethane
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-59cd1762050e40bd89eae69b47e2109f
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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