Pyrrolidine → HCID 69490103, compound

HRID 968665Notes

Reaction equation

HRID 968665 reaction equation
[Br:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:5]2[C:10](Cl)=[CH:9][CH:8]=[N:7][C:6]=12.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[Br:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:5]2[C:10]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:9][CH:8]=[N:7][C:6]=12

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 85885309HCID 85885309, compound

Product 1

HCID 69490103HCID 69490103, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromo-7-chloro-2-phenylpyrazolo[1,5-α]pyrimidine (100 mg, 0.32 mmol) was dissolved in ethanol. To this solution was added pyrrolidine (0.5 mL) and the reaction mixture heated at reflux for 10 minutes. The resulting mixture was concentrated in vacuo, then dissolved in dichloromethane and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The resulting solid was crystallized from methanol to give 85 mg (77%) of 3-bromo-2-phenyl-7-pyrrolidin-1-ylpyrazolo[1,5-α]pyrimidine as a solid. 1H NMR (CDCl3):δ 8.17 (m, 3H), 7.50 (m, 3H), 5.80 (d, 1H), 4.09 m (broad s, 4H), 2.10 (broad s, 4H); MS m/z 343 (M+1).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 10 minutes
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. dissolutiondissolved in dichloromethane
  5. washthe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was crystallized from methanol

Sources & evidence

ORD record
ord-5bd1ab990d674de69778a220700f0cfc
Source dataset
uspto-grants-2007_12
Patent number
US07304068B2

Reaction notes

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