Ammonium Chloride → 3-(4-((6-Amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylurea

HRID 626522Notes

Reaction equation

HRID 626522 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[C:14]([CH3:22])=[N:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=2)[CH:9]=[CH:8][N:7]=1)=[O:4].[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:19][C:16]1[N:15]=[C:14]([CH3:22])[C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[N:2]([CH3:23])[CH3:1])[CH:11]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 904098671,1-Dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea

Product 1

HCID 904098553-(4-((6-Amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylureaYield 113%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (0.500 g, 1.576 mmol) and NH4Cl (2.53 g, 47.3 mmol) in MeOH (10 mL) and THF (10 mL) was treated with zinc dust (1.030 g, 15.76 mmol) and stirred at RT for 0.5 h. The mixture was diluted with EtOAc, the solids removed via filtration, washed with EtOAc and the filtrate concentrated to dryness. The residue was treated with DCM, sonicated, the solids removed via filtration and the filtrate concentrated to dryness to afford 3-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylurea (510 mg, 113%). MS (ESI) m/z: 288.1 (M+H+).

Workup

  1. customthe solids removed via filtration
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated to dryness
  4. additionThe residue was treated with DCM
  5. customsonicated
  6. customthe solids removed via filtration
  7. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-8043326d56624ce383c966b7357af6c7
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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