HCID 53629213, compound → HCID 53629214, compound

HRID 1924345Notes

Reaction equation

HRID 1924345 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[CH:11]=[C:4]2[N:3]=1>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[CH:11]=[C:4]2[N:3]=1

Participants

4

Reactant 1

HCID 53629213HCID 53629213, compound

Product 1

HCID 53629214HCID 53629214, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5,7-dichloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine x272 (26.7 mmol, 1 eq., 6.08 g) in 125 ml of AcOH is added Zn powder (0.107 mol, 4 eq, 6.97 g). The mixture is then stirred for 48 hours at room temperature. After this time, the solvent is evaporated under reduce pressure and the reaction mixture poured on water, quenched with NaHCO3, and extracted with dichloromethane. The organic layer is dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product is purified by chromatography on silicagel (CH2Cl2/hexane: 50/50) to afford 5-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine x274 as a solid (3.60 g).

Workup

  1. customAfter this time, the solvent is evaporated
  2. additionthe reaction mixture poured on water
  3. customquenched with NaHCO3
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product is purified by chromatography on silicagel (CH2Cl2/hexane: 50/50)

Sources & evidence

ORD record
ord-59ba21fcf62348209ff5fa86d0b239bc
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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