Nitric Acid → HCID 178433718, compound

HRID 487293Notes

Reaction equation

HRID 487293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[N:16][C:17](=[O:18])[C:12]2=[C:11]([CH3:25])[NH:10]1.[N+:26]([O-])([OH:28])=[O:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:26]([O-:28])=[O:27])=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[N:16][C:17](=[O:18])[C:12]2=[C:11]([CH3:25])[NH:10]1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178433709HCID 178433709, compound

Product 1

HCID 178433718HCID 178433718, compoundYield 99%

Conditions

Temperature
-10 °C

Procedure

To a solution of 90% nitric acid (30 ml) at -10° C. was added in portions over 4 hours 1-(2-chlorophenylmethyl)-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one (4.9 g, 0.014 mol). The mixture was stirred at -10° C. for 30 minutes and poured into ice-water. The product was collected by filtration and washed with water. The solid residue was dissolved in methanol/DMF (3/1), treated with charcoal and the solvent was concentrated in vacuo. Ether was added to the residue and the product was collected by filtration and washed with ether to afford 5.5 g (99%) of 1-(2-chloro-5-nitrophenylmethyl)-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one as an off-white powder, m.p. 290°-1° C. when dried at 80° C. in high vacuum.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with water
  3. dissolutionThe solid residue was dissolved in methanol/DMF (3/1)
  4. additiontreated with charcoal
  5. concentrationthe solvent was concentrated in vacuo
  6. additionEther was added to the residue
  7. filtrationthe product was collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-e815cddf063f4228bd06fc807a71adca
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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