Methyl iodide → Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

HRID 2272678Notes

Reaction equation

HRID 2272678 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][C:3]=1[F:22].[H-].[Na+].[CH3:25]I>C1COCC1>[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N:14]([CH3:25])[C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][C:3]=1[F:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44184952HCID 44184952, compound

Product 1

HCID 44184953Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-carbamate (6a) (480 mg, 1.6 mmol) was dissolved in dry THF (8 mL) and cooled at 0° C. Sodium hydride (60% in mineral oil, 80 mg, 2.0 mmol) was added, and the reaction mixture was stirred for 40 minutes at 0° C. Methyl iodide (130 μL, 1.8 mmol) was added at 0° C. The ice bath was removed, and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated and the residue partitioned between DCM and distilled water. The organic layer was dried and evaporated, and the residue washed with diethyl ether to afford the title compound as a brown solid.

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe solvent was evaporated
  4. customthe residue partitioned between DCM
  5. distillationdistilled water
  6. customThe organic layer was dried
  7. customevaporated
  8. washthe residue washed with diethyl ether

Sources & evidence

ORD record
ord-4c39f5d9f96943498afaf75ed55f763b
Source dataset
uspto-grants-2015_09
Patent number
US09120789B2

Reaction notes

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