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

HRID 2278921Notes

Reaction equation

HRID 2278921 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[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.[Zn]>[NH2:19][C:16]1[N:15]=[CH:14][C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:22])[CH:11]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 904108451,1-Dimethyl-3-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea

Product 1

HCID 904106873-(4-((6-Aminopyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylureaYield 98.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethyl-3-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (0.631 g, 2.081 mmol) in MeOH (20 mL) was treated with NH4Cl (3.34 g, 62.4 mmol) followed by zinc dust (1.361 g, 20.81 mmol) and stirred at RT overnight. The solids were removed via filtration, washed with THF and the filtrate concentrated to dryness to afford 3-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylurea (560 mg, 98%). MS (ESI) m/z: 274.1 (M+H+).

Workup

  1. customThe solids were removed via filtration
  2. washwashed with THF
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-371933a6aaee4fd09447f75b09191cd5
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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