Water → N2-Methylpyridine-2,6-diamine

HRID 577320Notes

Reaction equation

HRID 577320 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9]([O-])([O-])=O.[K+].[K+].CI.O>C1COCC1>[CH3:9][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 88612,6-DiaminopyridineHCID 11430Potassium Carbonate

Product 1

HCID 55281082N2-Methylpyridine-2,6-diamineYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-diaminopyridine (10 g, 91.63 mmol) in dry THF (100 mL) was added K2CO3 (18.8 g, 136.23 mmol) and CH3I (13 g, 91.63 mmol) and the reaction mixture was stirred at room temperature for 16 h. Water was added (10 mL) and the mixture was extracted with EtOAc (100 mL). The EtOAc layer was dried and was concentrated under reduced pressure. The residue was further purified by column chromatography (SiO2, 60-120, chloroform) to give 2-methylamino-6-aminopyridine (1.1 g, 10%) as a brown solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (100 mL)
  2. dry with materialThe EtOAc layer was dried
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was further purified by column chromatography (SiO2, 60-120, chloroform)

Sources & evidence

ORD record
ord-ade1abf3ede54fb393984d5aea9ced0f
Source dataset
uspto-grants-2015_05
Patent number
US09040541B2

Reaction notes

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