Acetic Acid → HCID 15838382, compound

HRID 487284Notes

Reaction equation

HRID 487284 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[N:13][C:14]([NH2:15])=[C:9]3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:22]Br.[OH-].[NH4+].C(O)(=O)C>O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=4)=[N:13][C:14]([NH2:15])=[C:9]3[C:8]([Br:22])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 24408Bromine2×HCID 15838397HCID 15838397, compound

Product 1

HCID 15838382HCID 15838382, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1-cyclopentyl-6-(4-pyridyl)-pyrazolo(3,4-d)pyrimidin-4-amine (3.0 g, 0.011 mole) in water 60 ml) at room temperature was added bromine (1.8 g, 0.011 mol). The reaction mixture was stirred at room temperature for 1 hour, then was heated on a steam bath for 2 hours. The solvent was removed in vacuo and the residue was suspended in water. Ammonium hydroxide was added followed by acetic acid until a pH of 4-5 was obtained. A solid was collected by filtration and washed with water. Water (60 ml) and bromine (0.3 ml, 0.006 mol) were added to the solid residue and the mixture was heated on a steam bath for 1 hour. The mixture was poured into ice-water and ammonium hydroxide, then acetic acid was added. A solid was collected by filtration, dissolved in ethyl acetate, dried over MgSO4 and concentrated in vacuo to afford 2.2 g (56%) of 1-cyclopentyl-3-bromo-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine, m.p. 189°-191° C.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. customThe solvent was removed in vacuo
  3. additionAmmonium hydroxide was added
  4. customwas obtained
  5. filtrationA solid was collected by filtration
  6. washwashed with water
  7. temperaturethe mixture was heated on a steam bath for 1 hour
  8. filtrationA solid was collected by filtration
  9. dissolutiondissolved in ethyl acetate
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ddeb49f1aa9428e9dc493437f65eb55
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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