Ethylenediamine → N-(2,5-Dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamine

HRID 1016461Notes

Reaction equation

HRID 1016461 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([CH3:12])[CH:3]=1.[CH2:13]([NH2:16])[CH2:14][NH2:15].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:11][C:9]1[CH:10]=[C:6]2[N:5]=[C:4]([CH3:12])[CH:3]=[C:2]([NH:15][CH2:14][CH2:13][NH2:16])[N:7]2[N:8]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 184069877-Chloro-2,5-dimethylpyrazolo(1,5-a)pyrimidine

Product 1

HCID 18406994N-(2,5-Dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamineYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 7-chloro-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (3.0 g, 16.5 mmol) in ethanol (60 mL) was added ethylene diamine (4 mL, 60 mmol). After refluxing 18 hours the reaction was cooled, poured into saturated aqueous sodium bicarbonate, and then washed with ethyl acetate. The aqueous layer was then extracted with 3:7 isopropyl alcohol/chloroform, the combined extracts were dried (Na2SO4) and then concentrated under reduced pressure to give the title compound as an amorphous brown solid (3.2 g, 94%): +APcI MS (M+1)+ 206; 1H NMR (methanol-d4) δ: 6.05 (s, 1H), 6.00 (s, 1H), 3.45 (m, 2H), 2.91 (m, 2H).

Workup

  1. temperatureAfter refluxing 18 hours the reaction
  2. temperaturewas cooled
  3. washwashed with ethyl acetate
  4. extractionThe aqueous layer was then extracted with 3:7 isopropyl alcohol/chloroform
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90f310a4376644af9f2c95c18f2ef731
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

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