4-Pyridinecarboxaldehyde → HCID 178433705, compound

HRID 487251Notes

Reaction equation

HRID 487251 reaction equation
[CH:1]1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9]([CH3:16])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:17]1[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([N:7]2[C:11]3=[N:12][C:23]([C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)=[N:15][C:13](=[O:14])[C:10]3=[C:9]([CH3:16])[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 19432808HCID 19432808, compound

Product 1

HCID 178433705HCID 178433705, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Cyclohexyl-3-methyl-5-amino-1H-pyrazole-4-carboxamide (1.2 g, 5.4 mmol), 4-pyridinecarboxaldehyde (0.87 g, 8.1 mmol), toluene (125 ml) and p-toluenesulfonic acid monohydrate were combined and heated to reflux for 24 hours. The solvent was removed in vacuo and the residue was poured into water (450 ml). The obtained precipitate was collected by filtration, recrystallized from isopropanol (200 ml) and dried for 24 hours in high vacuum to afford 0.53 g (32%) of 1-cyclohexyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one as a cream colored solid, m.p. 292°-293° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was removed in vacuo
  4. additionthe residue was poured into water (450 ml)
  5. filtrationThe obtained precipitate was collected by filtration
  6. customrecrystallized from isopropanol (200 ml)
  7. customdried for 24 hours in high vacuum

Sources & evidence

ORD record
ord-045b5d86251a4c16a298344adb1a42a8
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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