Isonicotinic Acid → HCID 13745536, compound

HRID 568333Notes

Reaction equation

HRID 568333 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[C:22](O)(=O)[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>P(Cl)(Cl)(Cl)=O>[CH3:15][N:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:5]=[C:4]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:3]=[C:2]3[C:7]=2[NH:8][C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[N:1]3)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 13933224HCID 13933224, compound

Product 1

HCID 13745536HCID 13745536, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To 80 ml of phosphorus oxychloride are added 4 g of 4,5-diamino-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine and 1.7 g of isonicotinic acid, and the mixture is refluxed with heating for 6 hours under stirring. The reaction solution is concentrated and 700 ml of water is added to the residual oil. The solution is neutralized with an ammonia solution and the crystals precipitated are filtered, and then washed with water. Recrystallization from a mixture of chloroform and methanol (2:1) gives 2.7 g of 6-(4-methyl-1-piperazinyl)-2-phenyl-8-(4-pyridyl)purine, melting at 333°-337° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 6 hours
  3. concentrationThe reaction solution is concentrated
  4. addition700 ml of water is added to the residual oil
  5. customthe crystals precipitated
  6. filtrationare filtered
  7. washwashed with water
  8. customRecrystallization
  9. additionfrom a mixture of chloroform and methanol (2:1)

Sources & evidence

ORD record
ord-692b7678f05b4d8eab574bfe7990f0e3
Source dataset
uspto-grants-1988_03
Patent number
US04728644

Reaction notes

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