Isonicotinic Acid → HCID 13607464, compound

HRID 568330Notes

Reaction equation

HRID 568330 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[N:5]=[CH:4][N:3]=1.[C:14](O)(=O)[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1>P(Cl)(Cl)(Cl)=O>[CH2:10]([N:9]([CH2:12][CH3:13])[C:6]1[N:5]=[CH:4][N:3]=[C:2]2[C:7]=1[NH:8][C:14]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[N:1]2)[CH3:11]

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 13607463HCID 13607463, compound

Product 1

HCID 13607464HCID 13607464, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture obtained by grinding homogeneously 5 g of 4,5-diamino-6-diethylaminopyrimidine and 3.4 g of isonicotinic acid in a mortar is added to 110 ml of phosphorus oxychloride under stirring, and refluxed with heating for 3 hours. The reaction solution is concentrated and 180 ml of water is added to the residual oil. The resulting solution is neutralized with an ammonia solution and the precipitated crystals are filtered and washed with water. Recrystallization from ethanol gives 3.4 g of 6-diethylamino-8-(4-pyridyl)purine, melting at 260°-262° C.

Workup

  1. customA mixture obtained
  2. temperaturerefluxed
  3. temperaturewith heating for 3 hours
  4. concentrationThe reaction solution is concentrated
  5. addition180 ml of water is added to the residual oil
  6. filtrationthe precipitated crystals are filtered
  7. washwashed with water
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0322b61f2d524e8ca93607ddda4fd9ce
Source dataset
uspto-grants-1988_03
Patent number
US04728644

Reaction notes

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