Trifluoroacetic acid → 5-Methoxy-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine

HRID 333970Notes

Reaction equation

HRID 333970 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[N:6]2[N:22]=[CH:23][CH:24]=[C:5]2[N:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[N:6]2[N:22]=[CH:23][CH:24]=[C:5]2[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691598tert-Butyl 4-(5-methoxy-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylate

Product 1

HCID 668357295-Methoxy-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidineYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-methoxy-pyrazolo[1,5-a]pyrimidin-7-yl)piperazine-1-carboxylate (1.186 g, 3.56 mmol) was stirred for 10 minutes at room temperature in a 1:1 mixture of dichloromethane and trifluoroacetic acid. The mixture was evaporated to dryness under reduced pressure, the residue was dissolved in water, the resulting solution was washed with dichloromethane, basified with 4M NaOH and extracted with dichloromethane (3×). The combined organic phases were washed with water, dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 624 mg of a solid (2.68 mmol, 75%). MS (APCI): m/z=234.1 [M+1]+.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washthe resulting solution was washed with dichloromethane
  4. extractionextracted with dichloromethane (3×)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1388f3308109409084b28a3e1040c2d9
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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