2,3-Diaminopyridine → 2-Amino-3-(2-methyl-6-methoxycarbonylaminobenzylamino)pyridine

HRID 2073801Notes

Reaction equation

HRID 2073801 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]([O:21][CH3:22])=[O:20])[C:11]=1[CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[C:7]([NH:8][CH2:12][C:11]2[C:14]([NH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=[CH:17][C:10]=2[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 11430Potassium CarbonateHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chloride

Product 1

HCID 144998172-Amino-3-(2-methyl-6-methoxycarbonylaminobenzylamino)pyridineYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3-diaminopyridine (1.09 g) in methanol (22 ml) was added 2-methyl-6-methoxycarbonylaminobenzyl chloride (2.14 g) and potassium carbonate (1.38 g) at room temperature and the mixture was stirred for 1.5 hours. The insoluble material was removed by filtration and methanol in the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (30 g) and eluted with a mixture of chloroform and methanol (100:1) to give a crystalline product. The crystals were triturated with diisopropyl ether to give 2-amino-3-(2-methyl-6-methoxycarbonylaminobenzylamino)pyridine (1.44 g).

Workup

  1. customThe insoluble material was removed by filtration and methanol in the filtrate
  2. customwas evaporated under reduced pressure
  3. washeluted with a mixture of chloroform and methanol (100:1)
  4. customto give a crystalline product
  5. customThe crystals were triturated with diisopropyl ether

Sources & evidence

ORD record
ord-b7bea896c17f40f2bd48d0a4b8c87862
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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