Ethylenediamine → HCID 22034136, compound

HRID 1634567Notes

Reaction equation

HRID 1634567 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:10]([CH3:20])[N:11]=[C:12]2[C:17](Cl)=[N:16][C:15]([CH3:19])=[N:14][C:13]=12.[CH2:21]([NH2:24])[CH2:22][NH2:23]>C(#N)C>[NH2:23][CH2:22][CH2:21][NH:24][C:17]1[C:12]2=[N:11][N:10]([CH3:20])[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])=[C:13]2[N:14]=[C:15]([CH3:19])[N:16]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 22034104HCID 22034104, compound

Product 1

HCID 22034136HCID 22034136, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-(2,6-dichlorophenyl)-7-chloro-2,5-dimethylpyrazolo[4,3-d]pyrimidine (652 mg, 2.0 mmol) in acetonitrile (50 mL) at 50° C., add ethylene diamine (2.4 g, 40 mmol) in one portion. Maintain the reaction at 50° C. for 2 h, cool to ambient temperature and remove the volatiles by evaporation. Partition the residue between CH2Cl2 (50 mL) and 1N NaOH (50 mL) and extract the aqueous layer with CH2Cl2 (2×30 mL). Wash the combined organic extracts with water (30 mL), brine (30 mL), dry over MgSO4 and evaporate to obtain the title compound.

Workup

  1. temperatureMaintain
  2. customthe reaction at 50° C. for 2 h
  3. customremove the volatiles
  4. customby evaporation
  5. customPartition the residue between CH2Cl2 (50 mL) and 1N NaOH (50 mL)
  6. extractionextract the aqueous layer with CH2Cl2 (2×30 mL)
  7. washWash the combined organic extracts with water (30 mL), brine (30 mL)
  8. dry with materialdry over MgSO4
  9. customevaporate

Sources & evidence

ORD record
ord-8dfd0a5c5a0a40feab40e09853e93cb6
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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