Isonicotinic Acid → HCID 13607466, compound

HRID 568332Notes

Reaction equation

HRID 568332 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]=[C:4]([CH3:14])[N:3]=1.[C:15](O)(=O)[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>P(Cl)(Cl)(Cl)=O>[CH2:10]([N:9]([CH2:12][CH3:13])[C:6]1[N:5]=[C:4]([CH3:14])[N:3]=[C:2]2[C:7]=1[NH:8][C:15]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[N:1]2)[CH3:11]

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 20150115HCID 20150115, compound

Product 1

HCID 13607466HCID 13607466, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A homogeneous mixture obtained by grinding 5 g of 4,5-diamino-6-diethylamino-2-methylpyrimidine 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 aqueous solution is neutralized with an ammonia solution and the crystals precipitated are filtered and purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent. Recrystallization from methanol gives 2.3 g of 6-diethylamino-2-methyl-8-(4-pyridyl)purine, melting at 228°-230° C.

Workup

  1. customA homogeneous 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. customthe crystals precipitated
  7. filtrationare filtered
  8. custompurified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent
  9. customRecrystallization from methanol

Sources & evidence

ORD record
ord-0f6872b9a184426584631539ecbc10bf
Source dataset
uspto-grants-1988_03
Patent number
US04728644

Reaction notes

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