Dimethyl Sulfoxide → HCID 19434373, compound

HRID 1735747Notes

Reaction equation

HRID 1735747 reaction equation
CS(C)=O.CC(C)([O-])C.[K+].[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>O>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)=[N:20][CH:21]=1)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 782402-Bromo-5-nitropyridineHCID 344373Pyrimidin-5-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19434373HCID 19434373, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 7 ml of dimethyl sulfoxide was added 0.69 g (6.15 mmol) of potassium tert-butoxide, and 468 mg (4.92 mmol) of 5-aminopyrimidine was added to the solution while cooling with water. After stirring at room temperature for 1 hour, 500 mg (2.46 mmol) of 2-bromo-5-nitropyridine was added thereto under cooling with water, followed by further stirring at room temperature for 30 minutes. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, and the washing was adjusted to pH 8.5 with a 1 N sodium hydroxide aqueous solution and again extracted with ethyl acetate. The organic layer was combined with the above obtained organic layer, washed successively with water and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (eluting solvent: chloroform-methanol). The resulting crude crystals were washed with ethyl ether to obtain 0.32 g (1.47 mmol) of 5-[N-(5-nitro-2-pyridyl)amino]pyrimidine.

Workup

  1. additionwas added to the solution
  2. stirringby further stirring at room temperature for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1 N hydrochloric acid
  5. extractionagain extracted with ethyl acetate
  6. washwashed successively with water
  7. dry with materiala saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluting solvent: chloroform-methanol)
  10. washThe resulting crude crystals were washed with ethyl ether

Sources & evidence

ORD record
ord-0230fb1504474e3ea1329dd79c9de6b5
Source dataset
uspto-grants-1996_07
Patent number
US05538976

Reaction notes

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