Ammonium Chloride → Tert-butyl (4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)carbamate

HRID 626570Notes

Reaction equation

HRID 626570 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:23]([O-])=O)[N:3]=1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:23][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH:10]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 131735225Tert-butyl (4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamate

Product 1

HCID 131735226Tert-butyl (4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)carbamateYield 100%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl (4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamate (0.438 g, 1.265 mmol) and NH4Cl (2.029 g, 37.9 mmol) in MeOH (10 mL) and THF (10 mL) was treated with zinc dust (0.827 g, 12.65 mmol) and stirred at RT overnight. The mixture was diluted with EtOAc, the solids removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate concentrated to dryness to afford crude tert-butyl (4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)carbamate (100% yield assumed) which was used without further purification. MS (ESI) m/z: 317.2 (M+H+).

Workup

  1. customthe solids removed via filtration through diatomaceous earth
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-6892ae8274ec437f9c57a48e8cb78e1d
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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