Sodium Hydroxide → N-(2-Methyl-5-nitrophenyl)-4,5'-bipyrimidine-2-amine

HRID 2368777Notes

Reaction equation

HRID 2368777 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)=O.[N+]([O-])(O)=O.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[NH:28][C:29]([NH2:31])=[NH:30].[OH-].[Na+]>C(O)(C)C>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[NH:28][C:29]1[N:31]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[N:11][CH:12]=2)[CH:4]=[CH:3][N:30]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23073502HCID 23073502, compoundHCID 178426711HCID 178426711, compound

Product 1

HCID 23073521N-(2-Methyl-5-nitrophenyl)-4,5'-bipyrimidine-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2E)-3-(Dimethylamino)-1-pyrimidin-5-ylprop-2-en-1-one (1 g, 5.6 mmol) and N-(2-methyl-5-nitrophenyl)guanidine nitrate (1.44 g, 5.6 mmol) (Z. Szakacs et al., J. Med. Chem. 2005, 48, 249) were suspended in 20 mL of isopropanol. Sodium hydroxide (0.28 g, 7 mmol) was then added. The mixture solution was stirred overnight and cooled to room temperature. The solid was collected by filtration and rinsed with isopropanol and diethyl ether. The filtrate was concentrated under reduced pressure and the residue was dissolved in 15 mL of isopropanol. The solution obtained was refluxed overnight and cooled to room temperature. The solid was collected by filtration and rinsed with isopropanol and diethyl ether. The pooled solid was rinsed with water and diethyl ether, and dried in vacuum to obtain 1.2 g (70% yield) of the title compound. MS (M+1)=309.10.

Workup

  1. filtrationThe solid was collected by filtration
  2. washrinsed with isopropanol and diethyl ether
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 15 mL of isopropanol
  5. customThe solution obtained
  6. temperaturewas refluxed overnight
  7. temperaturecooled to room temperature
  8. filtrationThe solid was collected by filtration
  9. washrinsed with isopropanol and diethyl ether
  10. washThe pooled solid was rinsed with water and diethyl ether
  11. customdried in vacuum

Sources & evidence

ORD record
ord-71abe65d709f4536a25fada68886a2ab
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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