Water → HCID 20161365, compound

HRID 247046Notes

Reaction equation

HRID 247046 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:14])[N:9]([CH2:11][CH:12]=[CH2:13])[CH2:10][C:6]=2[N:5]=[C:4]2[N:15]([CH2:18][CH2:19]Cl)[N:16]=[CH:17][C:3]=12.N12CCCN=C1CCCCC2.O>CN(C=O)C>[NH2:1][C:2]1[C:7]2[C:8](=[O:14])[N:9]([CH2:11][CH:12]=[CH2:13])[CH2:10][C:6]=2[N:5]=[C:4]2[N:15]([CH:18]=[CH2:19])[N:16]=[CH:17][C:3]=12

Participants

5

Reactant 3

HCID 962Water2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20161367HCID 20161367, compound

Product 1

HCID 20161365HCID 20161365, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-amino-1-(2-chloroethyl)-6,7-dihydro-6-(2-propenyl)pyrazolo[3.4-b]pyrrolo[3,4-e]pyridin-5(1H)-one (15.69 g.) in dry DMF (65 ml.) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (9.65 ml.). The mixture was heated to 110° under nitrogen with stirring for five hours. After cooling, the mixture was poured into water (400 ml.) and the product was extracted into dichloromethane. The extract was washed with brine, dried (Na2SO4) and evaporated at reduced pressure to afford a suspension of crude product in DMF. This was warmed to effect complete dissolution, and water (350 ml.) was added to precipitate the product. After cooling to 0° , the precipitated solid was collected by filtration, washed with water, and dried in vacuo at 50° . In this manner there was obtained 11.09 grams of 4-amino-6,7-dihydro6-(2-propenyl)-1-vinylpyrazolo[3,4-b]pyrrolo[3,4-e]pyridin-5(1H)-one as a light yellow solid: m.p. 190°-191°.

Workup

  1. temperatureThe mixture was heated to 110° under nitrogen
  2. temperatureAfter cooling
  3. extractionthe product was extracted into dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated at reduced pressure
  7. customto afford
  8. temperatureThis was warmed
  9. additionwas added
  10. customto precipitate the product
  11. temperatureAfter cooling to 0°
  12. filtrationthe precipitated solid was collected by filtration
  13. washwashed with water
  14. customdried in vacuo at 50°

Sources & evidence

ORD record
ord-789b6780448743828f2d04d318cfc176
Source dataset
uspto-grants-1987_11
Patent number
US04705793

Reaction notes

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