Acetic Acid → HCID 15838383, compound

HRID 1736575Notes

Reaction equation

HRID 1736575 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.[N+:22]([O-])([OH:24])=[O:23].C(O)(=O)C>S(=O)(=O)(O)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]([N+:22]([O-:24])=[O:23])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 15838397HCID 15838397, compound

Product 1

HCID 15838383HCID 15838383, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-cyclopentyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine (4.6 g, 0.016 mol) in sulfuric acid (60 ml) in an ice-bath was added dropwise 70% nitric acid (36.8 ml). The reaction mixture was warmed to room temperature, stirred for 30 minutes then heated on a steam bath for 3/4 hour. The reaction mixture was added to ice-water/50% sodium hydroxide and the pH was adjusted to 4-5 with acetic acid. The product was collected by filtration and washed with water. The solid residue was purified by preparative thin layer chromatography on silica eluting with ethyl acetate (100%) to afford, after recrystallization from ethyl acetate, 0.81 g (16%) of 1-cyclopentyl-3-nitro-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine, m.p. 239°-241° C. when dried for 16 hours at 110° C. in high vacuum.

Workup

  1. temperaturethen heated on a steam bath for 3/4 hour
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customThe solid residue was purified by preparative thin layer chromatography on silica eluting with ethyl acetate (100%)
  5. customto afford
  6. customafter recrystallization from ethyl acetate, 0.81 g (16%) of 1-cyclopentyl-3-nitro-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine, m.p. 239°-241° C. when
  7. customdried for 16 hours at 110° C. in high vacuum

Sources & evidence

ORD record
ord-46031cc5977a4b69becc7fa9ce31037e
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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