Hydrochloric Acid → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 1920038Notes

Reaction equation

HRID 1920038 reaction equation
[Na].O=[C:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:4][CH:5]=O.Cl.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[NH:24][C:25]([NH2:27])=[NH:26]>C(O)(C)C.C1(C)C=CC=CC=1>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[NH:24][C:25]1[N:27]=[C:3]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:4]=[CH:5][N:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 43114742HCID 43114742, compoundHCID 178426708HCID 178426708, compound

Product 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

Under inert atmosphere, 5 g of sodium salt of the β-oxo-3-pyridinepropanal, with HPLC purity of 99% (A %) and salt content of 25% (residue by calcination), and 8 mL hydrochloric acid in isopropanol in 50 mL toluene is suspended. 3.7 g (2-methyl-5-nitrophenyl)guanidine is added, and the mixture is stirred at room temperature for an hour. The mixture is refluxed for 18 hours, removing the water with a Dean Stark apparatus. Once completed the conversion, the suspension is cooled to 10° C., and the precipitate is filtrated; this is crushed in warm water, yielding, upon filtration and drying, 2.5 g of product with HPLC purity of 96% (A %), identified through GC-MS.

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. customremoving the water with a Dean Stark apparatus
  3. temperaturethe suspension is cooled to 10° C.
  4. filtrationthe precipitate is filtrated
  5. customthis is crushed in warm water
  6. customyielding, upon filtration
  7. customdrying

Sources & evidence

ORD record
ord-223935cc5710448195d315903f702fc1
Source dataset
uspto-grants-2012_05
Patent number
US08168787B2

Reaction notes

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