Phenyl Methylcarbamate → HCID 21054849, compound

HRID 2376818Notes

Reaction equation

HRID 2376818 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[N:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:20][NH:21][C:22](=O)[O:23]C1C=CC=CC=1>CN(C)C=O>[CH3:20][NH:21][C:22]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:14]=[C:15]([NH2:19])[N:16]=[CH:17][N:18]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)=[O:23]

Participants

5

Reactant 3

HCID 16034Phenyl MethylcarbamateHCID 24758Sodium hydrideHCID 219492665-(6-Amino-pyrimidin-4-yloxy)-1H-indole

Product 1

HCID 21054849HCID 21054849, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (199 mg, 4.97 mmol) was suspended in N,N-dimethylformamide (10 ml) under nitrogen atmosphere, 6-(1H-indol-5-yloxy)pyrimidin-4-ylamine (1.07 g, 4.73 mmol) synthesized in Production example 2-2 was gradually added while the reaction mixture was stirred at room temperature. After 30 minutes, the reaction mixture was cooled with an ice water bath, then phenyl N-methylcarbamate (751 mg, 4.97 mmol) synthesized in Production example 2-1 was added. The reaction mixture was heated to room temperature and stirred for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and was dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent; ethyl acetate) to yield the title compound (847 mg, 2.99 mmol, 63%) as white crystals.

Workup

  1. additionwas gradually added while the reaction mixture
  2. temperaturethe reaction mixture was cooled with an ice water bath
  3. additionwas added
  4. temperatureThe reaction mixture was heated to room temperature
  5. stirringstirred for 1 hour
  6. customThe reaction mixture was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-d3a1424c9c9c4bf1b61898bc27ed7591
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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