Potassium Carbonate → HCID 178433700, compound

HRID 1736579Notes

Reaction equation

HRID 1736579 reaction equation
[CH:1]1([N:5]2[C:9]3=[N:10][C:11]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:12][C:13](N)=[C:8]3[C:7]([CH3:21])=[N:6]2)[CH2:4][CH2:3][CH2:2]1.N([O-])=[O:23].[Na+].C([O-])([O-])=O.[K+].[K+]>S(=O)(=O)(O)O.O>[CH:1]1([N:5]2[C:9]3=[N:10][C:11]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:12][C:13](=[O:23])[C:8]3=[C:7]([CH3:21])[NH:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19432793HCID 19432793, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 178433700HCID 178433700, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-cyclobutyl-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine (1.5 g, 5.3 mmol) in 75% aqueous sulfuric acid (25 ml) cooled in an ice-bath was added sodium nitrite (4.0 g, 58.0 mmol) in water (3 ml). The reaction mixture was warmed to room temperature, stirred for 24 hours and then warmed to 50° C. for 2 hours. The mixture was cooled in an ice-bath and sodium nitrite (4.2 g, 61.0 mmol) in water (5 ml) was added. The reaction mixture was warmed to room temperature and stirred for 24 hours. The mixture was poured onto ice-water and neutralized with K2CO3. The product was collected by filtration and recrystallized from isopropanol to afford 1.2 g (81%) of 1-cyclobutyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one as an off-white powder, m.p. 289°-90° C. when dried at 45° C. in high vacuum.

Workup

  1. temperaturewarmed to 50° C. for 2 hours
  2. temperatureThe mixture was cooled in an ice-bath
  3. temperatureThe reaction mixture was warmed to room temperature
  4. stirringstirred for 24 hours
  5. filtrationThe product was collected by filtration
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-326674acaf864a2ba215a9c360434ef2
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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