Nitric Acid → HCID 178433716, compound

HRID 487292Notes

Reaction equation

HRID 487292 reaction equation
[C:1]1([CH2:7][N:8]2[C:12]3=[N:13][C:14]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[N:15][C:16](=[O:17])[C:11]3=[C:10]([CH3:24])[NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+].[N+:27]([O-])([OH:29])=[O:28]>>[N+:27]([C:4]1[CH:3]=[CH:2][C:1]([CH2:7][N:8]2[C:12]3=[N:13][C:14]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)=[N:15][C:16](=[O:17])[C:11]3=[C:10]([CH3:24])[NH:9]2)=[CH:6][CH:5]=1)([O-:29])=[O:28]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 178433708HCID 178433708, compound

Product 1

HCID 178433716HCID 178433716, compoundYield 91%

Conditions

Temperature
0 °C

Procedure

To a solution of 90% nitric acid (30 ml) at -12°-0° C. was added in small portions 1-phenylmethyl-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one (2.99 g, 9.4 mmol). The reaction mixture was stirred at 0° C. for 2.5 hours and then poured slowly into ice-water. The solution was neutralized with concentrated ammonium hydroxide to afford a yellow solid which was collected by filtration and washed with water, ethanol and finally ether. The product was recrystallized from ethyl acetate/ethanol (3×) to afford 3.2 g (91%) of 1-(4-nitrophenylmethyl)-3-methyl-6-(4-pyridyl)pyrazolo(3,4-d)pyrimidin-4-one as a white powder which is contaminated with a small amount of the meta isomer (ratio para/meta is 93/7). The mixture had a melting point of 275°-281° C. when dried at 125° C. for 24 hours in high vacuum.

Workup

  1. customto afford a yellow solid which
  2. filtrationwas collected by filtration
  3. washwashed with water, ethanol and finally ether
  4. customThe product was recrystallized from ethyl acetate/ethanol (3×)

Sources & evidence

ORD record
ord-11e5813a59474eb3858fc0b0ef7d220d
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

Loading…