Acetic Acid → HCID 178463989, compound

HRID 1736576Notes

Reaction equation

HRID 1736576 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:14][C:15](N)=[C:10]2[C:9]([CH3:23])=[N:8]1)[CH3:2].N([O-])=[O:27].[Na+].[OH-].[NH4+].C(O)(=O)C>S(=O)(=O)(O)O.O>[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:14][C:15](=[O:27])[C:10]2=[C:9]([CH3:23])[NH:8]1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 19432770HCID 19432770, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178463989HCID 178463989, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(3-diethylaminopropyl)-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine in 50% sulfuric acid (25 ml) was cooled to 0° C. and stirred for 1 hour. A solution of sodium nitrite (0.78 g, 11.4 mmol) in water (5-7 ml) was added and the reaction mixture was stirred at 0° C. for 4 hours, then at room temperature for 24 hours. The reaction mixture was poured onto ice-water, treated with ammonium hydroxide and the pH adjusted to 7 with acetic acid. The aqueous layer was extracted with chloroform (4×250 ml) and the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was recrystallized in tert-butylmethyl ether/chloroform to afford 0.51 g (66%) of 1-(3-diethylaminopropyl)-3-methyl-6-(4-pyridyl)pyrazolo-[3,4-d]pyrimidin-4-one- 1/2 hydrate as an off-white powder, m.p. 164°-166° C. when dried at 80° C. for 16 hours in high vacuum.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 4 hours
  2. waitat room temperature for 24 hours
  3. additionThe reaction mixture was poured onto ice-water
  4. extractionThe aqueous layer was extracted with chloroform (4×250 ml)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized in tert-butylmethyl ether/chloroform

Sources & evidence

ORD record
ord-d62d3b2ac37b475da9a2396d5f6efa9a
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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