Water → tert-Butyl (5-aminopyridin-2-yl)methylcarbamate

HRID 1108404Notes

Reaction equation

HRID 1108404 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22064440tert-butyl N-(5-aminopyridin-2-yl)carbamate

Product 1

HCID 21715784tert-Butyl (5-aminopyridin-2-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 12-2 (6.0 g, 22.0 mmol) in 50 mL DMF at 0° C. was added NaH gradually. After the mixture was stirred for 40 min, CH3I (3.4 g, 24.0 mmol) was added in one portion. The reaction mixture was stirred for 5 hr, treated with 300 mL water and extracted three times with ethyl ether. The combined organic layers were washed with brine and dried over Na2SO4. After solvent removal, the residue was purified by silica gel flash chromatography (CHCl3 /hexanes 6:1) to afford the desired product 12-3 as a solid.

Workup

  1. stirringThe reaction mixture was stirred for 5 hr
  2. extractionextracted three times with ethyl ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter solvent removal
  6. customthe residue was purified by silica gel flash chromatography (CHCl3 /hexanes 6:1)

Sources & evidence

ORD record
ord-a8b48e63c31448e9a467fabea9f8e69d
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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