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

HRID 626509Notes

Reaction equation

HRID 626509 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-bf408b2b8e1f4d528eced9093f56feb2
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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